Hydrochloric Acid → (S)-2-(4-(2-amino-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)-N-(3,4-dimethoxyphenyl)benzo[d]thiazole-6-carboxamide hydrochloride

HRID 447156Notes

Reaction equation

HRID 447156 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:11][C:12]([C:14]2[CH:45]=[CH:44][C:17]3[N:18]=[C:19]([N:21]4[CH2:26][CH2:25][N:24]([C:27](=[O:43])[C@@H:28]([NH:35]C(=O)OC(C)(C)C)[CH2:29][C:30]5[S:31][CH:32]=[CH:33][CH:34]=5)[CH2:23][CH2:22]4)[S:20][C:16]=3[CH:15]=2)=[O:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[ClH:46]>O1CCOCC1>[ClH:46].[NH2:35][C@@H:28]([CH2:29][C:30]1[S:31][CH:32]=[CH:33][CH:34]=1)[C:27]([N:24]1[CH2:25][CH2:26][N:21]([C:19]2[S:20][C:16]3[CH:15]=[C:14]([C:12]([NH:11][C:5]4[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=4)=[O:13])[CH:45]=[CH:44][C:17]=3[N:18]=2)[CH2:22][CH2:23]1)=[O:43]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67235777(S)-tert-butyl 1-(4-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate

Product 1

HCID 53235512(S)-2-(4-(2-amino-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)-N-(3,4-dimethoxyphenyl)benzo[d]thiazole-6-carboxamide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

(S)-tert-butyl 1-(4-(6-(3,4-dimethoxyphenylcarbamoyl)benzo[d]thiazol-2-yl)piperazin-1-yl)-1-oxo-3-(thiophen-2-yl)propan-2-ylcarbamate (0.95 g, 1.45 mmol) was dissolved in 1,4-dioxane (2 ml) and treated with 4M HCl in 1,4-dioxane (2 ml). The resulting mixture was stirred at room temperature overnight. The resulting solid was filtered and treated with 4M HCl in 1,4-dioxane (2 ml), again stirring overnight. The solid was filtered, dissolved in dichloromethane and washed with saturated NaHCO3 to yield the title compound as its corresponding free base. The free base was chromatographed eluting with dichloromethane/methanol/ammonium hydroxide to yield the free base as a residue. The free base residue (0.50 g, 0.91 mmol) was dissolved in dichloromethane (2 ml) and treated with 1M HCl in diethyl ether (0.91 ml, 0.91 mmol) and the resulting mixture stirred at room temperature for 2 h. The resulting solid was filtered, washed with diethyl ether (2×) and dried to yield (S)-2-(4-(2-amino-3-(thiophen-2-yl)propanoyl)piperazin-1-yl)-N-(3,4-dimethoxyphenyl)benzo[d]thiazole-6-carboxamide, as its corresponding hydrochloride salt.

Workup

  1. filtrationThe resulting solid was filtered
  2. additiontreated with 4M HCl in 1,4-dioxane (2 ml)
  3. stirringagain stirring overnight
  4. filtrationThe solid was filtered
  5. dissolutiondissolved in dichloromethane
  6. washwashed with saturated NaHCO3

Sources & evidence

ORD record
ord-84898cc8a73442a4a6f468a2a2a0403d
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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