Dimethylformamide → HCID 73387939, compound

HRID 1056569Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:16]([C:17]([C:19]4[C:20]([F:33])=[C:21]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:29])=[O:28])[CH:22]=[CH:23][C:24]=4[F:25])=[O:18])=[CH:15][NH:14][C:11]3=[N:12][CH:13]=2)=[CH:4][CH:3]=1.[OH-].[K+].[C:36]([O:41][CH2:42]Cl)(=[O:40])[CH:37]([CH3:39])[CH3:38].[CH3:44]N(C=O)C>CCOC(C)=O>[C:36]([O:41][CH:42]([N:14]1[C:11]2=[N:12][CH:13]=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:9]=[C:10]2[C:16]([C:17](=[O:18])[C:19]2[C:24]([F:25])=[CH:23][CH:22]=[C:21]([NH:26][S:27]([CH2:30][CH2:31][CH3:32])(=[O:28])=[O:29])[C:20]=2[F:33])=[CH:15]1)[CH3:44])(=[O:40])[CH:37]([CH3:39])[CH3:38]

Participants

Conditions

Temperature: 10 °C

Procedure

To a mixture of N-(3-(5-(4-chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)propane-1-sulfonamide (0.5 g, 1.02 mmol) and potassium hydroxide (115 mg, 2.04 mmol) in anhydrous DMF (4 mL) was added a solution of chloromethyl isobutyrate (37 mg, 0.25 mmol) in anhydrous DMF (1 mL) over 30 min at 10° C. The reaction was stirred at 10° C. for 3 h, then diluted with EtOAc (40 mL) and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=5/1 to 4/1) to afford the title compound as a white solid (0.39 g, 63.3%). The title compound was characterized by LC-MS and 1H NMR as shown below:

Workup

filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by a silica gel column chromatography (PE/EtOAc (v/v)=5/1 to 4/1)

Sources & evidence

ORD record: ord-140129dc83744ef395ba5cd00a598b28
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09399639B2

Reaction notes

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