Hydrazine hydrate (1:1) → HCID 59694164, compound

HRID 899663Notes

Reaction equation

HRID 899663 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]([CH2:31][CH2:32][CH2:33][CH2:34][N:35]1C(=O)C2C(=CC=CC=2)C1=O)[CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[C:24]([O:29][CH3:30])[C:23]=2[CH2:22][CH2:21][CH2:20]1)=O)(C)(C)C.O.NN>C(O)C>[NH: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]([CH:19]1[C:28]2[N:27]=[CH:26][CH:25]=[C:24]([O:29][CH3:30])[C:23]=2[CH2:22][CH2:21][CH2:20]1)[CH2:31][CH2:32][CH2:33][CH2:34][NH2:35]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69293999HCID 69293999, compound

Product 1

HCID 59694164HCID 59694164, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-{[[4-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-(4-methoxy-5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-methyl}-benzimidazole-1-carboxylic acid tert-butyl ester (0.133 g, 0.22 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 crude material by column chromatography on silica gel (10:1:1 CH2Cl2—CH3OH—NH4OH) provided 56 mg (68%) 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 crude material by column chromatography on silica gel (10:1:1 CH2Cl2—CH3OH—NH4OH)

Sources & evidence

ORD record
ord-f6597cdb849d409f80517a9fca08449e
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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