Dimethylformamide → HCID 86714748, compound

HRID 2171859Notes

Reaction equation

HRID 2171859 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, compound2×

Product 1

HCID 86714748HCID 86714748, compound

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-ylamino)-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-174a749655e54541a42ae5fac070f531
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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