Trifluoroacetic acid → HCID 90314279, compound

HRID 1523875Notes

Reaction equation

HRID 1523875 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[N:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]([S:27]([NH:30]C(C)(C)C)(=[O:29])=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][C:16]=2[F:35])=[CH:11][N:10]=1>>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C:9]1[N:10]=[CH:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[C:22]([S:27]([NH2:30])(=[O:29])=[O:28])=[CH:23][CH:24]=[CH:25][CH:26]=3)=[CH:17][C:16]=2[F:35])=[CH:13][N:14]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90313289HCID 90313289, compound

Product 1

HCID 90314279HCID 90314279, compoundYield 59%

Procedure

Trifluoroacetic acid (1 mL) was added to neat 4′-(2-aminopyrimidin-5-yl)-N-(tert-butyl)-3′-fluoro-[1,1′-biphenyl]-2-sulfonamide (52 mg, 0.13 mmol). After 4 hours, the resulting solution was concentrated to dryness and purified by HPLC to provide the title compound (33 mg, 59%) as a clear glassy solid. MS (ESI): mass calcd. for C16H13FN4O2S, 344.07; m/z found, 345.0 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 8.54 (d, J=1.3, 2H), 8.05 (dd, J=7.8, 1.4, 1H), 7.70-7.56 (m, 3H), 7.40-7.28 (m, 5H), 7.03 (s, 2H).

Workup

  1. concentrationthe resulting solution was concentrated to dryness
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-da577251b96e4dc2a4e0eceb3ef8d928
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

Loading…