Ammonium Hydroxide → N-{3-[2-(1-amino-1-methylethyl)-5-(2-amino-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide

HRID 1962069Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C:13]([NH:16]C(=O)OC(C)(C)C)([CH3:15])[CH3:14])=[N:10][C:9]=2[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][S:31]([C:34]3[C:39]([F:40])=[CH:38][CH:37]=[CH:36][C:35]=3[F:41])(=[O:33])=[O:32])[C:25]=2[F:42])[CH:5]=[CH:4][N:3]=1.[OH-].[NH4+:44]>>[NH2:16][C:13]([C:11]1[S:12][C:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH2:44])[N:7]=2)=[C:9]([C:24]2[C:25]([F:42])=[C:26]([NH:30][S:31]([C:34]3[C:35]([F:41])=[CH:36][CH:37]=[CH:38][C:39]=3[F:40])(=[O:33])=[O:32])[CH:27]=[CH:28][CH:29]=2)[N:10]=1)([CH3:15])[CH3:14]

Participants

Reactant 2

HCID 14923Ammonium Hydroxide

HCID 579900251,1-Dimethylethyl {1-[5-(2-chloro-4-pyrimidinyl)-4-(3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-1,3-thiazol-2-yl]-1-methylethyl}carbamate

Product 1

HCID 57989657N-{3-[2-(1-amino-1-methylethyl)-5-(2-amino-4-pyrimidinyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamideYield 45%

Procedure

Following a procedure analogous to the procedure described in Example 312 using 1,1-dimethylethyl {1-[5-(2-chloro-4-pyrimidinyl)-4-(3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-1,3-thiazol-2-yl]-1-methylethyl}carbamate (100 mg, 0.156 mmol) and ammonium hydroxide (2 mL, 51.4 mmol) at 90° C. for 3 hours, the title compound was obtained as a solid (37 mg 45% yield). MS (ESI): 521.2 [M+H]+

Sources & evidence

ORD record: ord-2333e1eeb86f41a8918783eabfa6502e
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415345B2

Reaction notes

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