Methanesulfonyl chloride → N2-[5-(5-[(methylsulfonyl)amino]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-yl]-N-(2,2,2-trifluoroethyl)valinamide

HRID 510210Notes

Reaction equation

HRID 510210 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[C:13]([NH:17][C@H:18]([C:22]([NH:24][CH2:25][C:26]([F:29])([F:28])[F:27])=[O:23])[CH:19]([CH3:21])[CH3:20])[CH:14]=[N:15][CH:16]=3)=[CH:9][N:8]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:5]2=[N:6][CH:7]=1.[CH3:38][S:39](Cl)(=[O:41])=[O:40]>C(Cl)Cl.N1C=CC=CC=1>[CH3:38][S:39]([NH:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:12]=[C:13]([NH:17][C@H:18]([C:22]([NH:24][CH2:25][C:26]([F:29])([F:28])[F:27])=[O:23])[CH:19]([CH3:21])[CH3:20])[CH:14]=[N:15][CH:16]=3)=[CH:9][N:8]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[C:5]2=[N:6][CH:7]=1)(=[O:41])=[O:40]

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 131733259N2-{5-[5-(amino)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl]pyridin-3-yl}-N-(2,2,2-trifluoroethyl)valinamide

Product 1

HCID 131733261N2-[5-(5-[(methylsulfonyl)amino]-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-yl]-N-(2,2,2-trifluoroethyl)valinamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of N2-[5-(5-amino-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-3-yl]-N-(2,2,2-trifluoroethyl)valinamide 5-1b (50 mg, 0.093 mmol) in DCM (2 mL) and pyridine (0.5 mL) was added methanesulfonyl chloride (7.62 μl, 0.098 mmol) and mixture was stirred for 18 h. The residue 5-3a was used without further purification. MS APCI: [M+H]+ m/z=615.1.

Workup

  1. customThe residue 5-3a was used without further purification

Sources & evidence

ORD record
ord-511d0ad03a074c19a6e340dd43f6c1f5
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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