Methanesulfonyl chloride → 1-{3-[4-Amino-7-(1-methanesulfonyl-piperidin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl]-phenyl}-3-(3,5-dichloro-phenyl)-urea

HRID 916790

Reaction equation

HRID 916790 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:14]=[C:15]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=4)=[O:21])[CH:16]=[CH:17][CH:18]=3)=[O:12])=[CH:9][N:8]([CH:31]3[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]3)[C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>CN(C=O)C.C(Cl)Cl>[NH2:1][C:2]1[C:3]2[C:10]([C:11]([C:13]3[CH:14]=[C:15]([NH:19][C:20]([NH:22][C:23]4[CH:28]=[C:27]([Cl:29])[CH:26]=[C:25]([Cl:30])[CH:24]=4)=[O:21])[CH:16]=[CH:17][CH:18]=3)=[O:12])=[CH:9][N:8]([CH:31]3[CH2:32][CH2:33][N:34]([S:38]([CH3:37])(=[O:40])=[O:39])[CH2:35][CH2:36]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 672198621-[3-(4-Amino-7-piperidin-4-yl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-3-(3,5-dichloro-phenyl)-urea

Product 1

HCID 672188321-{3-[4-Amino-7-(1-methanesulfonyl-piperidin-4-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl]-phenyl}-3-(3,5-dichloro-phenyl)-ureaYield 19%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

A solution of 1-[3-(4-Amino-7-piperidin-4-yl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonyl)-phenyl]-3-(3,5-dichloro-phenyl)-urea (100 mg, 0.19 mmol) and methanesulfonylchloride (22 mg, 0.19 mmol) in DMF/CH2Cl2 (2/3, 5 mL) was stirred in a sealed tube for 1.5 hours at room temperature. The reaction mixture concentrated in vacuo. Purification by reverse phase preparative HPLC (HPLC method 2) provided the title compound as a white solid (21.8 mg, 19%). MS: 603.5 (MH+); HPLC Rf: 2.3 min. (HPLC method 2); HPLC purity: 100%.

Workup

  1. concentrationThe reaction mixture concentrated in vacuo
  2. customPurification by reverse phase preparative HPLC (HPLC method 2)

Sources & evidence

ORD record
ord-fc6577b2e84144dca34199561fe47c15
Source dataset
uspto-grants-2007_09
Patent number
US07271262B2

Linked notes

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