Hydrochloric Acid → 3-(2-{(S)-4-[2-(3-Fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-piperazin-2-yl}-acetylamino)-2,2-dimethyl-propionamide

HRID 1963073Notes

Reaction equation

HRID 1963073 reaction equation
Cl.O1CCOCC1.C(OC([N:15]1[CH2:20][CH2:19][N:18]([C:21]([C:23]2[N:31]3[C:26]([CH:27]=[CH:28][CH:29]=[CH:30]3)=[C:25]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:24]=2[CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[C:40]=2[CH3:46])=[O:22])[CH2:17][C@@H:16]1[CH2:47][C:48](=[O:57])[NH:49][CH2:50][C:51]([C:54](=[O:56])[NH2:55])([CH3:53])[CH3:52])=O)(C)(C)C>C(Cl)Cl>[F:45][C:41]1[C:40]([CH3:46])=[C:39]([CH:44]=[CH:43][CH:42]=1)[CH2:38][C:24]1[C:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[C:26]2[N:31]([C:23]=1[C:21]([N:18]1[CH2:19][CH2:20][NH:15][C@@H:16]([CH2:47][C:48]([NH:49][CH2:50][C:51]([CH3:53])([CH3:52])[C:54]([NH2:55])=[O:56])=[O:57])[CH2:17]1)=[O:22])[CH:30]=[CH:29][CH:28]=[CH:27]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 67773127(S)-2-[(2-Carbamoyl-2-methyl-propylcarbamoyl)-methyl]-4-[2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 509065803-(2-{(S)-4-[2-(3-Fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-piperazin-2-yl}-acetylamino)-2,2-dimethyl-propionamideYield 83.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 4 N solution of hydrogen chloride in dioxane (0.68 ml, 2.71 mmol) was added to a solution of the compound of step 6 (0.185 g, 0.27 mmol) in 2.7 ml of anhydrous DCM and the mixture stirred at room temperature for 2.5 h. After evaporation of the solvents, the obtained solid was triturated with anhydrous diethyl ether/DCM (9:1) and dried in vacuo at 45° C. to give 0.131 g of the title compound in the form of 3-(2-{(S)-4-[2-(3-fluoro-2-methyl-benzyl)-1-phenyl-indolizine-3-carbonyl]-piperazin-2-yl}-acetylamino)-2,2-dimethyl-propionamide hydrochloride as a light green powder with the following characteristics:

Workup

  1. customAfter evaporation of the solvents
  2. customthe obtained solid was triturated with anhydrous diethyl ether/DCM (9:1)
  3. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-a1b6e634fe054b4fa64165a01d253ded
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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