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 L-prolyl-L-alaninate hydrochloride

HRID 1968347Notes

Reaction equation

HRID 1968347 reaction equation
C(OC([N:8]1[CH2:58][CH2:57][CH2:56][C@H:9]1[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.Cl>ClCCl.C(OCC)C>[ClH:53].[NH:8]1[CH2:58][CH2:57][CH2:56][C@H:9]1[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: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:25][CH:26]=1)=[O:16])[CH3:14])=[O:11]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 687628552-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl 1-(tert-butoxycarbonyl)-L-prolyl-L-alaninate

Product 1

HCID 687640302-{4-(2-({(2-(4-Chlorophenyl)-1,3-thiazol-4-yl)methyl}sulfanyl)-3,5-dicyano-6-(pyrrolidin-1-yl)pyridin-4-yl)phenoxy}ethyl L-prolyl-L-alaninate hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

495 mg (0.588 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 1-(tert-butoxycarbonyl)-L-prolyl-L-alaninate were dissolved in 3 ml dichloromethane, and 5.876 ml of a 1N solution of hydrogen chloride in diethyl ether were added. After 6 hours of stirring, the precipitated solid was filtered off with suction, washed with diethyl ether and dried under reduced pressure. 410 mg (90% 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. custom410 mg (90% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-906978fbf793471ab604f2f5f7e37a82
Source dataset
uspto-grants-2013_04
Patent number
US08420825B2

Reaction notes

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