Water → HCID 58541772, compound

HRID 600259Notes

Reaction equation

HRID 600259 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[N:14]([C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[C:18](S(C)(=O)=O)[N:17]=2)[CH:13]=[CH:12][S:11]3)=[CH:4][CH:3]=1.[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([NH2:39])[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:28])[CH3:27].CCN(C(C)C)C(C)C.O>CS(C)=O>[C:26]([O:30][C:31]([N:33]1[CH2:38][CH2:37][CH:36]([NH:39][C:18]2[N:17]=[C:16]([C:15]3[N:14]4[C:10]([S:11][CH:12]=[CH:13]4)=[N:9][C:8]=3[C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[CH:21]=[CH:20][N:19]=2)[CH2:35][CH2:34]1)=[O:32])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 12682914-Amino-1-Boc-piperidineHCID 58541623HCID 58541623, compound

Product 1

HCID 58541772HCID 58541772, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 6-(4-fluorophenyl)-5-(2-methanesulfonyl-pyrimidin-4-yl)-imidazo[2,1-b]thiazole (L) (1.05 g, 2.8 mmol) in dimethylsulfoxide (12.0 mL) is added 4-amino-piperidine-1-carboxylic acid tert-butyl ester (1.12 g, 5.6 mmol) followed by Hunig's Base (0.76 mL, 5.6 mmol). The reaction mixture is sealed and set to shake at 100° C. for 12 hours. After cooling to room temperature, water is added (50 mL) and the aqueous phase extracted with ethyl acetate (4×20 mL). The combined organic phase is washed with a saturated, aqueous, sodium chloride solution (3×50 mL) and dried over anhydrous sodium sulfate. The organic phase is filtered and the solvent evaporated in vacuo. The crude product is purified by silica gel column chromatography eluting with ethyl acetate/hexane (3/2). The compound 4-{4-[6-(4-fluorophenyl)-imidazo[2,1-b]thiazol-5-yl]-pyrimidin-2-ylamino}-piperidine-1-carboxylic acid tert-butyl ester (M) (Compound CCXXXIII, Table 2) is obtained as a light yellow solid (1.2 g, 88%); m.p. 209-211° C.;

Workup

  1. customThe reaction mixture is sealed
  2. extractionthe aqueous phase extracted with ethyl acetate (4×20 mL)
  3. washThe combined organic phase is washed with a saturated, aqueous, sodium chloride solution (3×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationThe organic phase is filtered
  6. customthe solvent evaporated in vacuo
  7. customThe crude product is purified by silica gel column chromatography
  8. washeluting with ethyl acetate/hexane (3/2)

Sources & evidence

ORD record
ord-11ff39cae8564b7ab71073991641f3e3
Source dataset
uspto-grants-2011_03
Patent number
US07902192B2

Reaction notes

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