Cesium carbonate → tert-butyl (3R)-3-[[5-(5-cyano-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate

HRID 1507545Notes

Reaction equation

HRID 1507545 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[N:3]=[CH:2]1.I[C:13]1[C:14]([NH:27][C@@H:28]2[CH2:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]2)=[N:15][C:16]([N:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[N:17][C:18]=1[O:19][CH3:20].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu](I)I.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>[C:10]([C:8]1[CH:7]=[CH:6][C:5]2[S:1][C:2]([C:13]3[C:14]([NH:27][C@@H:28]4[CH2:33][CH2:32][CH2:31][N:30]([C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[CH2:29]4)=[N:15][C:16]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)=[N:17][C:18]=3[O:19][CH3:20])=[N:3][C:4]=2[CH:9]=1)#[N:11]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 107021045-BenzothiazolecarbonitrileHCID 89554305HCID 89554305, compound

Product 1

HCID 117686401tert-butyl (3R)-3-[[5-(5-cyano-1,3-benzothiazol-2-yl)-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

Following the same procedure as in step 3 of Example 121 using 1,3-benzothiazole-5-carbonitrile (56.1 mg, 0.35 mmol, 1.80 equiv), tert-butyl (3R)-3-[[5-iodo-6-methoxy-2-(morpholin-4-yl)pyrimidin-4-yl]amino]piperidine-1-carboxylate (100 mg, 0.19 mmol, 1.00 equiv), copper iodide (6.7 mg, 0.035 mmol, 0.18 equiv), cesium Carbonate (0.37 g, 6.00 equiv, 1.14 mmol) and Pd(PPh3)4 (40.4 mg, 0.035 mmol, 0.18 equiv) in DMF (6.0 mL). The crude product was purified by flash chromatography on silica gel, eluting with a mixture of 10-20% ethyl acetate in petroleum ether to give the title compound as a white solid. MS m/z [M+H]+ (ESI): 552.

Workup

  1. customThe crude product was purified by flash chromatography on silica gel
  2. washeluting with a mixture of 10-20% ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-33046ffc00a542da9c9c025694dd1f59
Source dataset
uspto-grants-2015_12
Patent number
US09221809B2

Reaction notes

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