Dimethylformamide → HCID 86714748, compound

HRID 1055063Notes

Reaction equation

HRID 1055063 reaction equation
C(Cl)(=O)C([Cl:4])=O.[F:7][C:8]1[C:9]([NH:34][C@@H:35]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:36][S:37](O)(=[O:39])=[O:38])=[CH:10][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=3)[N:16]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:15]=2)=[N:12][CH:13]=1.CN(C=O)C>ClCCl>[F:7][C:8]1[C:9]([NH:34][C@@H:35]([C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:36][S:37]([Cl:4])(=[O:39])=[O:38])=[CH:10][C:11]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=3)[N:16]([S:24]([C:27]3[CH:33]=[CH:32][C:30]([CH3:31])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH:15]=2)=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 86714749HCID 86714749, compound

Product 1

HCID 86714748HCID 86714748, compoundYield 111.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (3.5 mL, 38.7 mmol) was added to a solution of (S)-2-(5-fluoro-2-(5-fluoro-1-tosyl-1H-pyrrolo[2,3-b]pyridin-3yl)pyridin-4- lamino)-3,3-dimethylbutane-1-sulfonic acid, 57a, (7.3 g, 12.9 mmol) in dichloromethane (130 mL), followed by the slow, dropwise addition of DMF (2 mL). The yellow colored solution was stirred at room temperature for 1 hour. The solvent was removed under reduced pressure to afford 8.4 g of the desired product as a foamy yellow solid: LC/MS (60-90% ACN/water 5 min with 0.9% FA) m/z 585.72 (M+H) RT =2.30 minutes.

Workup

  1. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-0ed4926e6e284e7985c0776792cec46f
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

Loading…