HCID 90313198, compound → HCID 90312381, compound

HRID 1523967Notes

Reaction equation

HRID 1523967 reaction equation
[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([S:20]([NH:23]C(C)(C)C)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=3)=[C:10]([F:28])[C:9]=2[F:29])=[N:6][CH:7]=1>C(O)(C(F)(F)F)=O>[NH2:1][C:2]1[N:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[C:15]([S:20]([NH2:23])(=[O:21])=[O:22])=[CH:16][CH:17]=[CH:18][CH:19]=3)=[C:10]([F:28])[C:9]=2[F:29])=[N:6][CH:7]=1

Participants

3

Reactant 1

HCID 90313198HCID 90313198, compound

Product 1

HCID 90312381HCID 90312381, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 4′-(5-aminopyrazin-2-yl)-N-tert-butyl-2′,3′-difluorobiphenyl-2-sulfonamide (168 mg, 0.40 mmol) in TFA (3 mL) was heated at 50° Celsius for 3 hours. The reaction was then cooled to rt and carefully partitioned between NaHCO3 and EtOAc. The organic layer was isolated, dried over MgSO4, and concentrated to dryness. Purification by FCC afforded the title compound (140 mg, 96%). MS (ESI): mass calcd. for C16H12F2N4O2S, 362.06; m/z found, 363.1 [M+H]+. 1H NMR (500 MHz, DMSO-d6) δ 8.40 (s, 1H), 8.12-8.01 (m, 2H), 7.72-7.61 (m, 3H), 7.45-7.36 (m, 3H), 7.19 (m, 1H), 6.81 (s, 2H).

Workup

  1. temperatureThe reaction was then cooled to rt
  2. customcarefully partitioned between NaHCO3 and EtOAc
  3. customThe organic layer was isolated
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated to dryness
  6. customPurification by FCC

Sources & evidence

ORD record
ord-2983cd98e815420c8417378085672103
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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