HCID 57990021, compound → HCID 57989699, compound

HRID 1961970Notes

Reaction equation

HRID 1961970 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[S:12][CH:11]=[N:10][C:9]=2[C:13]2[CH:14]=[C:15]([NH:19][S:20]([C:23]3[C:28]([F:29])=[CH:27][CH:26]=[CH:25][C:24]=3[F:30])(=[O:22])=[O:21])[CH:16]=[CH:17][CH:18]=2)[CH:5]=[CH:4][N:3]=1>C(N)C(C)C>[F:30][C:24]1[CH:25]=[CH:26][CH:27]=[C:28]([F:29])[C:23]=1[S:20]([NH:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:9]2[N:10]=[CH:11][S:12][C:8]=2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:10][CH2:9][CH:13]([CH3:14])[CH3:18])[N:7]=2)[CH:14]=1)(=[O:22])=[O:21]

Participants

3

Reactant 1

HCID 57990021HCID 57990021, compound

Product 1

HCID 57989699HCID 57989699, compoundYield 130%

Reagents, catalysts & solvents 1

HCID 6558IsobutylamineSolvent

Conditions

Temperature
35 °C

Procedure

N-{3-[5-(2-Chloro-4-pyrimidinyl)-1,3-thiazol-4-yl]phenyl}-2,6-difluorobenzenesulfonamide (0.1 g, 0.2 mmol) was taken up in 2 mL isobutylamine and heated to 35° C. overnight. The solvent was removed in vacuo and the residue taken up in EtOAc and washed with 2 mL of 0.1 N HCl (aq). The organic layer was dried over Na2SO4 and evaporated to afford the title compound (65 mg, 0.130 mmol), 60.2% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.00 (s, 1H), 9.15 (s, 1H), 7.98 (d, J=5.1 Hz, 1H), 7.60-7.69 (m, 1H), 7.37 (t, J=5.9 Hz, 1H), 7.31 (t, J=7.9 Hz, 1H), 7.26 (s, 1H), 7.15-7.24 (m, 4H), 5.93-6.05 (m, 1H), 2.95-3.06 (m, 2H), 0.82 (d, J=6.6 Hz, 6H). MS (ESI): 501 [M+H]+.

Workup

  1. customThe solvent was removed in vacuo
  2. washwashed with 2 mL of 0.1 N HCl (aq)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-a303786301944d30b13d2c2162b6377d
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

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