Pyridine → HCID 68706378, compound

HRID 645526Notes

Reaction equation

HRID 645526 reaction equation
[CH2:1]([S:8](Cl)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][O:27][C:28]2[C:33]([NH2:34])=[C:32]([NH:35][CH2:36][CH:37]3[CH2:45][CH2:44][C:40]4([CH2:43][CH2:42][CH2:41]4)[CH2:39][CH2:38]3)[N:31]=[C:30]([C:46]#[N:47])[N:29]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].N1C=CC=CC=1>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][O:27][C:28]2[C:33]([NH:34][S:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)(=[O:10])=[O:9])=[C:32]([NH:35][CH2:36][CH:37]3[CH2:45][CH2:44][C:40]4([CH2:43][CH2:42][CH2:41]4)[CH2:39][CH2:38]3)[N:31]=[C:30]([C:46]#[N:47])[N:29]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 3

HCID 1049Pyridine2×HCID 74740Phenylmethanesulfonyl chloride2×HCID 68708811HCID 68708811, compound

Product 1

HCID 68706378HCID 68706378, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzylsulfonylchloride (0.50 mmol) is added to a solution of 4-(2-{5-amino-2-cyano-6-[(spiro[3.5]non-7-ylmethyl)amino]pyrimidin-4-yloxy}ethyl)piperidine-1-carboxylic acid t-butyl ester (167 mg) and pyridine (0.66 mmol) in CH2Cl2 (3 mL) are added at 0° C. After stirring at room temperature for 1 h, benzylsulfonylchloride (0.50 mmol), pyridine (0.66 mmol) and DMAP (catalytic amount) are added to the reaction mixture again. The reaction mixture is stirred at room temperature for 1 h and diluted with AcOEt. The organic layer is washed with H2O and evaporated in vacuo. The resulting residue is purified by silica gel column chromatography to give 4-(2-{2-cyano-5-phenylmethanesulfonylamino-6-[(spiro[3.5]non-7-ylmethyl)amino]pyrimidin-4-yloxy}ethyl)piperidine-1-carboxylic acid tert-butyl ester.

Workup

  1. additionare added at 0° C
  2. stirringThe reaction mixture is stirred at room temperature for 1 h
  3. washThe organic layer is washed with H2O
  4. customevaporated in vacuo
  5. customThe resulting residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2303000b172849f2bed22a8d6e6d7d2a
Source dataset
uspto-grants-2010_04
Patent number
US07704996B2

Reaction notes

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