Hydrochloric Acid → 2-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl beta-alanyl-L-alaninate hydrochloride

HRID 1968346Notes

Reaction equation

HRID 1968346 reaction equation
C(OC([NH:8][CH2:9][CH2:10][C:11]([NH:13][C@H:14]([C:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[C:33]([C:34]#[N:35])=[C:32]([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[N:31]=[C:30]([S:41][CH2:42][C:43]3[N:44]=[C:45]([C:48]4[CH:53]=[CH:52][C:51]([Cl:54])=[CH:50][CH:49]=4)[S:46][CH:47]=3)[C:29]=2[C:55]#[N:56])=[CH:24][CH:23]=1)=[O:17])[CH3:15])=[O:12])=O)(C)(C)C.Cl>ClCCl.C(OCC)C>[ClH:54].[NH2:8][CH2:9][CH2:10][C:11]([NH:13][C@H:14]([C:16]([O:18][CH2:19][CH2:20][O:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[C:33]([C:34]#[N:35])=[C:32]([N:36]3[CH2:40][CH2:39][CH2:38][CH2:37]3)[N:31]=[C:30]([S:41][CH2:42][C:43]3[N:44]=[C:45]([C:48]4[CH:49]=[CH:50][C:51]([Cl:54])=[CH:52][CH:53]=4)[S:46][CH:47]=3)[C:29]=2[C:55]#[N:56])=[CH:26][CH:27]=1)=[O:17])[CH3:15])=[O:12]

Participants

5

Reactant 2

HCID 313Hydrochloric Acid2×HCID 59435673HCID 59435673, compound

Product 1

HCID 687629002-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl beta-alanyl-L-alaninate hydrochlorideYield 82%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 6344DichloromethaneSolvent

Procedure

200 mg (0.245 mmol) of 2-{4-(2-({(2-(4-chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl N-(tert-butoxycarbonyl)-beta-alanyl-L-alaninate (Example 8A) were dissolved in 2 ml dichloromethane, and 2.45 ml 1M HCl in diethyl ether were added. After 3 hours, 1 ml of a 1N solution of hydrogen chloride in diethyl ether was added and the mixture was stirred at room temperature for a further 2 hours. The precipitated solid was filtered off with suction, washed with diethyl ether and dried under reduced pressure. 155 mg (yield: 82% of theory) of the target compound were obtained.

Workup

  1. filtrationThe precipitated solid was filtered off with suction
  2. washwashed with diethyl ether
  3. customdried under reduced pressure
  4. custom155 mg (yield: 82% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-6c7271f34e3545ffb7e249b3660287d3
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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