Ammonium Hydroxide → HCID 57989661, compound

HRID 239477Notes

Reaction equation

HRID 239477 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.[NH4+:31].[OH-]>>[NH2:31][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

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 57990021HCID 57990021, compound

Product 1

HCID 57989661HCID 57989661, compoundYield 64.7%

Conditions

Temperature
140 °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 NH4OH and heated to 140° C. for 20 min in a microwave reactor. The solvent was removed under reduced pressure and the residue was taken up in EtOAc and washed with 2 mL of 0.1 N HCl (aq). The organic layer was dried over Na2SO4 and evaporated onto silica gel. Purification by ISCO chromatography (0 to 50% EtOAC in DCM) afforded the title compound (62 mg, 0.139 mmol, 64.7% yield) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 11.00 (s, 1H), 9.16 (s, 1H), 7.94 (d, J=5.1 Hz, 1H), 7.59-7.69 (m, 1H), 7.32 (t, J=7.9 Hz, 1H), 7.16-7.27 (m, 5H), 6.78 (s, 2H), 5.99 (d, J=5.3 Hz, 1H). MS (ESI): 446 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. washwashed with 2 mL of 0.1 N HCl (aq)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. customevaporated onto silica gel
  5. customPurification by ISCO chromatography (0 to 50% EtOAC in DCM)

Sources & evidence

ORD record
ord-4ed8eaeaa2c1469ca7310c7bdf5ed5cf
Source dataset
uspto-grants-2014_02
Patent number
US08642759B2

Reaction notes

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