Hydrochloric Acid → 2-{(S)-4-[2-(3-Fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-piperazin-2-yl}-N-(tetrahydropyran-4-ylmethyl)-acetamide

HRID 1963066Notes

Reaction equation

HRID 1963066 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[N:24]3[C:19]([CH:20]=[CH:21][CH:22]=[CH:23]3)=[C:18]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:17]=2[CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=2[CH3:39])=[O:15])[CH2:10][C@@H:9]1[CH2:40][C:41](=[O:50])[NH:42][CH2:43][CH:44]1[CH2:49][CH2:48][O:47][CH2:46][CH2:45]1)=O)(C)(C)C.Cl.O1CCOCC1>C(Cl)Cl>[F:38][C:34]1[C:33]([CH3:39])=[C:32]([CH:37]=[CH:36][CH:35]=1)[CH2:31][C:17]1[C:18]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:19]2[N:24]([C:16]=1[C:14]([N:11]1[CH2:12][CH2:13][NH:8][C@@H:9]([CH2:40][C:41]([NH:42][CH2:43][CH:44]3[CH2:45][CH2:46][O:47][CH2:48][CH2:49]3)=[O:50])[CH2:10]1)=[O:15])[CH:23]=[CH:22][CH:21]=[CH:20]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 70663881(S)-4-[2-(3-Fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-2-{[(tetrahydropyran-4-ylmethyl)-carbamoyl]-methyl}-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 498552302-{(S)-4-[2-(3-Fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-piperazin-2-yl}-N-(tetrahydropyran-4-ylmethyl)-acetamideYield 71.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of step 3 (0.113 g, 0.17 mmol) in 1.65 ml of DCM cooled to 0° C. was added a 4 N solution of hydrogen chloride in dioxane (0.41 ml, 1.65 mmol). The mixture was stirred for 3 h at room temperature and then evaporated to dryness. The solid was triturated several times with diethyl ether and dried in vacuo at 40° C. to give 0.071 g of the title compound in the form of 2-{(S)-4-[2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-piperazin-2-yl}-N-(tetrahydropyran-4-ylmethyl)-acetamide hydrochloride with the following characteristics:

Workup

  1. customevaporated to dryness
  2. customThe solid was triturated several times with diethyl ether
  3. customdried in vacuo at 40° C.

Sources & evidence

ORD record
ord-50ca5544e25044ac9779d47857bb7a31
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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