Hydrochloric Acid → N-(3-{5-[2-({(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}amino)-pyrimidin-4-yl]imidazo[2,1-b][1,3]thiazol-6-yl}phenyl)glycinamide hydrochloride

HRID 1783815Notes

Reaction equation

HRID 1783815 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]2[N:19]=[C:20]3[N:24]([C:25]=2[C:26]2[CH:31]=[CH:30][N:29]=[C:28]([NH:32][C@@H:33]4[CH2:38][CH2:37][CH2:36][N:35]([S:39]([C:42]5[CH:47]=[CH:46][C:45]([Cl:48])=[CH:44][CH:43]=5)(=[O:41])=[O:40])[CH2:34]4)[N:27]=2)[CH:23]=[CH:22][S:21]3)[CH:13]=1)=[O:10])(C)(C)C.Cl>O1CCOCC1>[ClH:48].[Cl:48][C:45]1[CH:46]=[CH:47][C:42]([S:39]([N:35]2[CH2:36][CH2:37][CH2:38][C@@H:33]([NH:32][C:28]3[N:27]=[C:26]([C:25]4[N:24]5[C:20]([S:21][CH:22]=[CH:23]5)=[N:19][C:18]=4[C:14]4[CH:13]=[C:12]([NH:11][C:9](=[O:10])[CH2:8][NH2:7])[CH:17]=[CH:16][CH:15]=4)[CH:31]=[CH:30][N:29]=3)[CH2:34]2)(=[O:41])=[O:40])=[CH:43][CH:44]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57590777tert-butyl {2-[(3-{5-[2-({(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}amino)-pyrimidin-4-yl]imidazo[2,1-b][1,3]thiazol-6-yl}phenyl)amino]-2-oxoethyl}carbamate

Product 1

HCID 68799325N-(3-{5-[2-({(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}amino)-pyrimidin-4-yl]imidazo[2,1-b][1,3]thiazol-6-yl}phenyl)glycinamide hydrochlorideYield 201.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

The tert-butyl{2-[(3-{5-[2-({(3R)-1-[(4-chlorophenyl)sulfonyl]piperidin-3-yl}amino)-pyrimidin-4-yl]imidazo[2,1-b][1,3]thiazol-6-yl}phenyl)amino]-2-oxoethyl}carbamate (71 mg, 0.098 mmol) was dissolved in dioxane (3 ml) and treated with a 4N HCl solution in dioxane (1 ml). The mixture was stirred at room temperature for 3 hours. The volatiles were removed in vacuo and the residue was triturated in ether. Filtration afforded the title compound as a yellow solid (65 mg). M.p.=208-212° C. 400 MHz 1H NMR (DMSO-d6) δ: 10.69 (s, 1H), 8.18 (br. s, 3H), 8.13 (d, J=5.9 Hz, 1H), 7.88 (t, J=1.6 Hz, 1H), 7.79-7.75 (m, 2H), 7.71-7.66 (m, 3H), 7.48-7.43 (m, 2H), 7.34 (d, J=7.8 Hz, 1H), 6.45 (d, J=5.9 Hz, 1H), 5.15 (br. s, 3H), 4.04-3.95 (m, 1H), 3.79 (d, J=5.5 Hz, 2H), 3.70 (dd, J=11.3, 4.3 Hz, 1H), 3.48-3.41 (m, 1H), 2.57-2.48 (m, 1H), 2.42 (t, J=10.6 Hz, 1H), 1.95-1.82 (m, 2H), 1.67-1.54 (m, 1H), 1.48-1.37 (m, 1H). LCMS: 623 [M+H]. Calc. for C28H27N8O3S2Cl.2.52HCl: C, 47.03; H, 4.16; N, 15.67. Found C, 47.04; H, 3.97; N, 15.46.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was triturated in ether
  3. filtrationFiltration

Sources & evidence

ORD record
ord-d8a3ad10a4654756a8ddb4f676f9b8b7
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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