Hydrazine hydrate (1:1) → HCID 10237298, compound

HRID 1624294Notes

Reaction equation

HRID 1624294 reaction equation
C(OC([N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]=[C:9]1[CH2:17][N:18]([CH2:29][C:30]1([CH2:33][CH2:34][N:35]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:32][CH2:31]1)[CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)=O)(C)(C)C.O.NN>C(O)C>[NH2:35][CH2:34][CH2:33][C:30]1([CH2:29][N:18]([CH2:17][C:9]2[NH:8][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[N:10]=2)[CH:19]2[C:28]3[N:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH2:22][CH2:21][CH2:20]2)[CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69233093HCID 69233093, compound

Product 1

HCID 10237298HCID 10237298, compoundYield 51.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-{[{1-[2-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-ethyl]-cyclopropylmethyl}-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzimidazole-1-carboxylic acid tert-butyl ester (0.121 g, 0.20 mmol) in ethanol (4 mL) was added hydrazine monohydrate (0.20 mL, 4.12 mmol) and the resultant mixture was stirred at room temperature overnight. The mixture was filtered through filter paper and concentrated. Purification of the cnide material by column chromatography on silica gel (20:1:1 CH2Cl2—CH3OH—NH4OH) provided 39 mg (50%) of the free base of the title compound as a yellow oil.

Workup

  1. filtrationThe mixture was filtered
  2. filtrationthrough filter paper
  3. concentrationconcentrated
  4. customPurification of the cnide material by column chromatography on silica gel (20:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-07cea9c0cec9432cbe6f5c349df5d1fe
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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