Water → N-(3-{[6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl]amino}-2,2-dimethylpropyl)methanesulfonamide

HRID 2089004Notes

Reaction equation

HRID 2089004 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([CH3:14])([CH3:13])[CH2:11][NH2:12])[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH:3]=1.C(N(CC)CC)C.[CH3:31][S:32](Cl)(=[O:34])=[O:33].O>CN(C=O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]([CH3:14])([CH3:13])[CH2:11][NH:12][S:32]([CH3:31])(=[O:34])=[O:33])[CH:5]=[C:4]([C:15]2[C:23]3[C:18](=[N:19][CH:20]=[CH:21][CH:22]=3)[NH:17][CH:16]=2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chloride2×HCID 49830295N-[6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl]-2,2-dimethylpropane-1,3-diamine

Product 1

HCID 49830296N-(3-{[6-chloro-4-(1H-pyrrolo[2,3-b]pyridin-3-yl)pyridin-2-yl]amino}-2,2-dimethylpropyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 74 (70.0 mg, 0.212 mmol) in DMF (1 mL) was added triethylamine (0.089 mL, 0.64 mmol) and methanesulfonyl chloride (0.018 mL, 0.23 mmol). After 5 hours, more methanesulfonyl chloride (0.010 mL) was added. The reaction mixture was stirred overnight and treated with water slowly. The precipitate was filtered, washed with water, and oven dried to give the title compound. 1H NMR (300 MHz, DMSO-d6) ppm 0.92 (s, 6H), 2.81 (d, J=7.14 Hz, 2H), 2.87 (s, 3H), 3.15 (d, J=6.35 Hz, 2H), 6.79-7.02 (m, 4H), 7.22 (dd, J=7.93, 4.76 Hz, 1H), 8.15 (d, J=2.38 Hz, 1H), 8.28-8.37 (m, 2H), 12.16 (s, 1H). MS (ESI+) m/z 408.0 (M+H)+.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with water, and oven
  3. customdried

Sources & evidence

ORD record
ord-155e6d9910b5467d8aeba9e3550cf82b
Source dataset
uspto-grants-2013_05
Patent number
US08435980B2

Reaction notes

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