Trifluoroacetic acid → 2-[5-(tert-butylsulfamoyl)pyridin-2-yl]-1-cyclopentyl-5-fluoro-6-methyl-1H-indole-3-carboxamide

HRID 1028015Notes

Reaction equation

[C:1]([NH:5][S:6]([C:9]1[CH:10]=[N:11][C:12]([C:15]2[N:16]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[C:17]3[C:22]([C:23]=2[C:24]#[N:25])=[CH:21][C:20]([F:26])=[C:19]([CH3:27])[CH:18]=3)=[CH:13][CH:14]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=[O:34]>O>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[N:16]([CH:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[C:17]3[C:22]([C:23]=2[C:24]([NH2:25])=[O:34])=[CH:21][C:20]([F:26])=[C:19]([CH3:27])[CH:18]=3)=[N:11][CH:10]=1)(=[O:7])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

Into a solution of N-tert-butyl-6-(3-cyano-1-cyclopentyl-5-fluoro-6-methyl-1H-indol-2-yl)pyridine-3-sulfonamide (90 mg, 0.2 mmol) in TFA (2.0 mL) was added 2 drops of water. The mixture was stirred at 40° C. for 30 min and then evaporated. The residue was purified on silica gel eluting with 5 to 30% ethyl acetate in CH2Cl2 to provide the title compound (19 mg, 20%). MS m/z 473.3 M+H+; 1H NMR (500 MHz, DMSO-d6): δ 9.10 (1H, dd, J=2.0, 1.0 Hz), 8.29 (1H, dd, J=10.5, 2.5 Hz), 7.89 (1H, s), 7.81 (1H, dd, J=8.5, 1.0 Hz), 7.59 (1H, d, J=10.5 Hz), 7.49 (1H, d, J=6.5 Hz), 7.02 (2H, br s), 4.63-4.56 (1H, m), 2.46 (3H, s), 2.16-2.08 (2H, m), 1.96-1.85 (4H, m), 1.60-1.56 (2H, m), 1.17 (9H, s).

Workup

customevaporated
customThe residue was purified on silica gel eluting with 5 to 30% ethyl acetate in CH2Cl2

Sources & evidence

ORD record: ord-da44e0521712442fa847a173579e3298
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735414B2

Reaction notes

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