Hydrochloric Acid → Neladenoson dalanate hydrochloride

HRID 1968342Notes

Reaction equation

HRID 1968342 reaction equation
C(OC([NH:8][C@H:9]([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])[CH3:10])=O)(C)(C)C.Cl>ClCCl.C(OCC)C>[ClH:54].[NH2:8][C@H:9]([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])[CH3:10]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 594356502-{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-alaninate

Product 1

HCID 56848984Neladenoson dalanate hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

1.5 g (1.84 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-alaninate (Example 7A) were initially charged in 24 ml of dichloromethane. 18.37 ml of a 1N solution of hydrogen chloride in diethyl ether were added, and the reaction solution was then stirred at RT overnight. The solid formed was filtered off and washed with diethyl ether. This gave 1.44 g (97% of theory, purity about 94%) of the target compound.

Workup

  1. customThe solid formed
  2. filtrationwas filtered off
  3. washwashed with diethyl ether

Sources & evidence

ORD record
ord-ff4dcf1f2e84431092d24fbd3bfd36f4
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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