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 N-(tert-butoxycarbonyl)-L-alanyl-L-leucinate hydrochloride

HRID 1621345Notes

Reaction equation

HRID 1621345 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:13][C@H:14]([C:19]([O:21][CH2:22][CH2:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([C:31]2[C:36]([C:37]#[N:38])=[C:35]([N:39]3[CH2:43][CH2:42][CH2:41][CH2:40]3)[N:34]=[C:33]([S:44][CH2:45][C:46]3[N:47]=[C:48]([C:51]4[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=4)[S:49][CH:50]=3)[C:32]=2[C:58]#[N:59])=[CH:27][CH:26]=1)=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl>ClCCl.C(OCC)C.O1CCOCC1>[ClH:57].[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:13][C@H:14]([C:19]([O:21][CH2:22][CH2:23][O:24][C:25]1[CH:26]=[CH:27][C:28]([C:31]2[C:36]([C:37]#[N:38])=[C:35]([N:39]3[CH2:40][CH2:41][CH2:42][CH2:43]3)[N:34]=[C:33]([S:44][CH2:45][C:46]3[N:47]=[C:48]([C:51]4[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=4)[S:49][CH:50]=3)[C:32]=2[C:58]#[N:59])=[CH:29][CH:30]=1)=[O:20])[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 68764188HCID 68764188, compound

Product 1

HCID 687664932-{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)-L-alanyl-L-leucinate hydrochloride

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

153 mg (0.18 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)-L-alanyl-L-leucinate were dissolved in 5 ml dichloromethane and 5 ml diethyl ether. 4.5 ml (17.8 mmol) of 4M hydrogen chloride in dioxane were added, and the mixture was stirred at room temperature for 3 h. The precipitate was filtered off, washed with diethyl ether and dried under high vacuum. This gave 68 mg (55. % of theory) of the desired target compound.

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with diethyl ether
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-5cd89cce666a4c49b4cd4341885188db
Source dataset
uspto-grants-2014_07
Patent number
US08772498B2

Reaction notes

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