Ethanol → HCID 178521730, compound

HRID 1028215Notes

Reaction equation

HRID 1028215 reaction equation
C([O:3][C:4]([CH2:6][C:7](=O)[CH2:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([O:15][C:16]([N:18]2[CH2:27][CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([NH:28][C:29]([NH:31][C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=4[F:38])=[O:30])[CH:24]=3)[CH2:19]2)=[O:17])[CH2:11][CH2:10]1)=O)C.C(O)C.O.[NH2:44][NH2:45]>C(OC(C)C)(C)C>[OH:3][C:4]1[CH:6]=[C:7]([CH2:8][C@H:9]2[CH2:10][CH2:11][C@H:12]([O:15][C:16]([N:18]3[CH2:19][CH2:20][C:25]4[C:26](=[CH:21][CH:22]=[C:23]([NH:28][C:29]([NH:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[F:38])=[O:30])[CH:24]=4)[CH2:27]3)=[O:17])[CH2:13][CH2:14]2)[NH:44][N:45]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)2×HCID 178472213HCID 178472213, compound

Product 1

HCID 178521730HCID 178521730, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

To a mixture of trans-6-[3-(2-fluoro-phenyl)-ureido]-3,4-dihydro-1H-isoquinoline-2-carboxylic acid 4-(3-ethoxycarbonyl-2-oxo-propyl)-cyclohexyl ester (189 mg) obtained in Example (42a) and ethanol (5 mL), hydrazine monohydrate (0.022 mL) was added at 0° C. During the reaction, hydrazine monohydrate was further added thereto, and the mixture was stirred until the reaction substrate was consumed. The reaction mixture was concentrated and purified by column chromatography (dichloromethane/methanol) to obtain a white solid. This white solid was vigorously stirred in isopropyl ether and collected by filtration to obtain the title compound (90 mg, 51%) as a white solid.

Workup

  1. additionwas added at 0° C
  2. additionwas further added
  3. customwas consumed
  4. concentrationThe reaction mixture was concentrated
  5. custompurified by column chromatography (dichloromethane/methanol)
  6. customto obtain a white solid
  7. filtrationcollected by filtration

Sources & evidence

ORD record
ord-98c39ac53f4e4a09a34d19a55be0636d
Source dataset
uspto-grants-2014_05
Patent number
US08735425B2

Reaction notes

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