Hydrochloric Acid → (2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)-N-hydroxyacrylamide hydrochloride

HRID 226470Notes

Reaction equation

HRID 226470 reaction equation
Cl.[Cl:2][C:3]1[CH:33]=[CH:32][C:6]([C:7]([N:9]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[S:16][CH:17]=[C:18](/[CH:20]=[CH:21]/[C:22]([NH:24][O:25]C4CCCCO4)=[O:23])[N:19]=3)[CH2:10]2)=[O:8])=[CH:5][CH:4]=1.C(OCC)C>CO>[ClH:2].[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:7]([N:9]2[CH2:13][CH2:12][CH:11]([NH:14][C:15]3[S:16][CH:17]=[C:18](/[CH:20]=[CH:21]/[C:22]([NH:24][OH:25])=[O:23])[N:19]=3)[CH2:10]2)=[O:8])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86603627(2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide

Product 1

HCID 86603776(2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)-N-hydroxyacrylamide hydrochlorideYield 155.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10% Metallic hydrogen chloride (1.4 mL) was added to the solution of (2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)-N-(tetrahydro-2H-pyran-2-yloxy)acrylamide (0.6 g) in MeOH (12 ml) and the mixture was stirred at ambient temperature for 3.5 hours. To the reaction mixture was added ethyl ether and isolated precipitate was collected by filtration to give (2E)-3-(2-{[1-(4-chlorobenzoyl)-3-pyrrolidinyl]amino}-1,3-thiazol-4-yl)-N-hydroxyacrylamide hydrochloride (0.42 g)

Workup

  1. customisolated precipitate
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-7c4aed9560ee460ea3c50561d63a5870
Source dataset
uspto-grants-2009_07
Patent number
US07557127B2

Reaction notes

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