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-((2S)-2,4-diaminobutanoyl)-L-alaninate dihydrochloride

HRID 1968349Notes

Reaction equation

HRID 1968349 reaction equation
C(OC([NH:8][C@@H:9]([CH2:56][CH2:57][NH:58]C(OC(C)(C)C)=O)[C:10]([NH:12][C@H:13]([C:15]([O:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[C:32]([C:33]#[N:34])=[C:31]([N:35]3[CH2:39][CH2:38][CH2:37][CH2:36]3)[N:30]=[C:29]([S:40][CH2:41][C:42]3[N:43]=[C:44]([C:47]4[CH:52]=[CH:51][C:50]([Cl:53])=[CH:49][CH:48]=4)[S:45][CH:46]=3)[C:28]=2[C:54]#[N:55])=[CH:23][CH:22]=1)=[O:16])[CH3:14])=[O:11])=O)(C)(C)C.[ClH:66]>ClCCl.C(OCC)C>[ClH:53].[ClH:66].[NH2:8][C@@H:9]([CH2:56][CH2:57][NH2:58])[C:10]([NH:12][C@H:13]([C:15]([O:17][CH2:18][CH2:19][O:20][C:21]1[CH:22]=[CH:23][C:24]([C:27]2[C:32]([C:33]#[N:34])=[C:31]([N:35]3[CH2:36][CH2:37][CH2:38][CH2:39]3)[N:30]=[C:29]([S:40][CH2:41][C:42]3[N:43]=[C:44]([C:47]4[CH:48]=[CH:49][C:50]([Cl:53])=[CH:51][CH:52]=4)[S:45][CH:46]=3)[C:28]=2[C:54]#[N:55])=[CH:25][CH:26]=1)=[O:16])[CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86643857HCID 86643857, compound

Product 1

HCID 687653402-{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-((2S)-2,4-diaminobutanoyl)-L-alaninate dihydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

420 mg (0.444 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-{(2S)-2,4-bis((tert-butoxycarbonyl)-amino)butanoyl}-L-alaninate were dissolved in 5 ml dichloromethane, and 4.442 ml of a 1N solution of hydrogen chloride in diethyl ether were added. After 4 hours of stirring, the precipitated solid was filtered off with suction, washed with diethyl ether and dried under reduced pressure. 322 mg (88% 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. custom322 mg (88% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-2b170d9ad5b146c78b495917dc7db676
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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