Hydrochloric Acid → N-{3-[5-{2-[(2-Aminoethyl)amino]-4-pyrimidinyl}-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamide

HRID 590203Notes

Reaction equation

HRID 590203 reaction equation
Cl.O1CCOCC1.CC([N:12]([CH2:16][CH2:17][NH:18][C:19]1[N:24]=[C:23]([C:25]2[S:29][C:28]([C:30]([CH3:33])([CH3:32])[CH3:31])=[N:27][C:26]=2[C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([NH:40][S:41]([C:44]3[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=3[F:51])(=[O:43])=[O:42])[C:35]=2[F:52])[CH:22]=[CH:21][N:20]=1)C(=O)[O-])(C)C.CO>C(Cl)Cl>[NH2:12][CH2:16][CH2:17][NH:18][C:19]1[N:24]=[C:23]([C:25]2[S:29][C:28]([C:30]([CH3:33])([CH3:31])[CH3:32])=[N:27][C:26]=2[C:34]2[C:35]([F:52])=[C:36]([NH:40][S:41]([C:44]3[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=3[F:51])(=[O:42])=[O:43])[CH:37]=[CH:38][CH:39]=2)[CH:22]=[CH:21][N:20]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 312751,4-DioxaneHCID 867130171,1-Dimethylethyl[2-({4-[4-(3-{[(2,5-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-2-(1,1-dimethylethyl)-1,3-thiazol-5-yl]-2-pyrimidinyl}amino)ethyl]carbamate

Product 1

HCID 57989685N-{3-[5-{2-[(2-Aminoethyl)amino]-4-pyrimidinyl}-2-(1,1-dimethylethyl)-1,3-thiazol-4-yl]-2-fluorophenyl}-2,5-difluorobenzenesulfonamideYield 117.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4N solution of HCl in 1,4-dioxane (1.7 ml, 7.1 mmol) was added to a stirring solution of 1,1-dimethylethyl[2-({4-[4-(3-{[(2,5-difluorophenyl)sulfonyl]amino}-2-fluorophenyl)-2-(1,1-dimethylethyl)-1,3-thiazol-5-yl]-2-pyrimidinyl}amino)ethyl]carbamate (0.31 g, 0.47 mmol) (composite batches prepared as described in the previous step) in DCM (10 ml) at rt. MeOH (1 ml) was added to aid in solubility. The reaction was allowed to stir at rt for 3 h. The volatiles were removed and the residue was dried in vacuo to afford the title compound of Step B (0.31 g, quantitative yield) as a hydrochloride salt that was used without further purification; 1H NMR (400 MHz, DMSO-d6) δ ppm 10.77 (s, 1H), 7.93-8.18 (m, 4H), 7.20-7.69 (m, 7H), 3.37-3.53 (m, 2H), 2.96 (d, J=5.1 Hz, 2H), 1.41 (s, 9H). MS (ES+): 563 [M+H]+.

Workup

  1. customprepared
  2. customat rt
  3. customThe volatiles were removed
  4. customthe residue was dried in vacuo

Sources & evidence

ORD record
ord-00c01928e1d645d187abf07f5c10daf3
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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