Acetyl chloride → N-(3-(2-(4-(1H-1,2,3-triazol-1-yl)phenylamino)pyrimidin-4-yl)-5-morpholinophenyl)acetamide

HRID 40737Notes

Reaction equation

HRID 40737 reaction equation
C(Cl)(=[O:3])C.[N:5]1([C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17]3[N:22]=[C:21]([C:23]4[CH:28]=[C:27]([NH:29][C:30]5[CH:35]=CC=CC=5)[CH:26]=[C:25]([N:36]5[CH2:41][CH2:40][O:39][CH2:38][CH2:37]5)[CH:24]=4)[CH:20]=[CH:19][N:18]=3)=[CH:12][CH:11]=2)[CH:9]=[CH:8][N:7]=[N:6]1>C(Cl)Cl>[N:5]1([C:10]2[CH:11]=[CH:12][C:13]([NH:16][C:17]3[N:22]=[C:21]([C:23]4[CH:28]=[C:27]([NH:29][C:30](=[O:3])[CH3:35])[CH:26]=[C:25]([N:36]5[CH2:37][CH2:38][O:39][CH2:40][CH2:41]5)[CH:24]=4)[CH:20]=[CH:19][N:18]=3)=[CH:14][CH:15]=2)[CH:9]=[CH:8][N:7]=[N:6]1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 59588088N-(4-(1H-1,2,3-triazol-1-yl)phenyl)-4-(3-morpholino-5-(phenylamino)phenyl)pyrimidin-2-amine

Product 1

HCID 59588168N-(3-(2-(4-(1H-1,2,3-triazol-1-yl)phenylamino)pyrimidin-4-yl)-5-morpholinophenyl)acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of acetyl chloride (0.02 mL, 0.28 mmol) in CH2Cl2 (1 mL) was added to N-(4-(1H-1,2,3-triazol-1-yl)phenyl)-4-(3-morpholino-5-(phenylamino)phenyl)pyrimidin-2-amine (0.11 g, 0.28 mmol) in CH2Cl2 (3 mL) drop wise at 0° C. The reaction was warmed to room temperature, stirred for 30 min, concentrated, and purified by chromatography on silica gel (ethyl acetate/hexanes) to afford N-(3-(2-(4-(1H-1,2,3-triazol-1-yl)phenylamino)pyrimidin-4-yl)-5-morpholinophenyl)acetamide. MS (ESI) 457 (M+H).

Workup

  1. concentrationconcentrated
  2. custompurified by chromatography on silica gel (ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2f02ec5fdfad473081383ec04df1dbfe
Source dataset
uspto-grants-2013_09
Patent number
US08530480B2

Reaction notes

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