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Cesium carbonate → (3R)-tert-butyl 3-(6-methoxy-2-morpholino-5-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)pyrimidin-4-ylamino)piperidine-1-carboxylate

HRID 1507519
Notes
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Reaction equation

HRID 1507519 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[CH:4]=[CH:5][C:6]2[S:10][CH:9]=[N:8][C:7]=2[CH:11]=1.I[C:15]1[C:16]([NH:29][CH:30]2[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31]2)=[N:17][C:18]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)=[N:19][C:20]=1[O:21][CH3:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:22][O:21][C:20]1[N:19]=[C:18]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:17]=[C:16]([NH:29][C@@H:30]2[CH2:35][CH2:34][CH2:33][N:32]([C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[CH2:31]2)[C:15]=1[C:9]1[S:10][C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:12])[F:13])=[CH:11][C:7]=2[N:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 199372475-(Trifluoromethyl)-1,3-benzothiazoleHCID 117677619Tert-butyl 3-((5-iodo-6-methoxy-2-morpholinopyrimidin-4-yl)amino)piperidine-1-carboxylate

Product 1

HCID 89554303(3R)-tert-butyl 3-(6-methoxy-2-morpholino-5-(5-(trifluoromethyl)benzo[d]thiazol-2-yl)pyrimidin-4-ylamino)piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 178418397HCID 178418397, compoundCatalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

Into a 25-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen was placed a solution of 5-(trifluoromethyl)-1,3-benzothiazole (100 mg, 0.49 mmol, 1.80 equiv) in N,N-dimethylformamide (5.0 mL), tert-butyl 3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (140.2 mg, 0.27 mmol, 1.00 equiv), Cesium Carbonate (534.3 mg, 6.00 equiv), Tetrakis(triphenylphosphine)palladium (57.8 mg, 0.05 mmol, 0.18 equiv), and Copper (I) iodide (9.5 mg, 0.05 mmol, 0.18 equiv). The resulting mixture was heated for 2.5 h at 85° C. in an oil bath, cooled down, quenched by the addition of 15 mL of water and then extracted with ethyl acetate (4×15 mL). The combined organic layers were washed with brine (20 mL) and dried over anhydrous sodium sulfate. After filtration and concentration under reducing pressure, the residue was purified by chromatography on a silica gel column eluting with petroleum ether/ethyl acetate (10:1-3:1) to afford the title compound as a gray white solid. MS m/z [M+H]+ (ESI): 595

Workup

  1. customInto a 25-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperaturecooled down
  4. customquenched by the addition of 15 mL of water
  5. extractionextracted with ethyl acetate (4×15 mL)
  6. washThe combined organic layers were washed with brine (20 mL)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationAfter filtration and concentration
  9. customthe residue was purified by chromatography on a silica gel column
  10. washeluting with petroleum ether/ethyl acetate (10:1-3:1)

Sources & evidence

ORD record
ord-6ae727363e0647b1b0aacfa0f26fcb90
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09221809B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes