Hydrazine hydrate (1:1) → HCID 10286988, compound

HRID 1624321Notes

Reaction equation

HRID 1624321 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]([CH2:30][CH2:31][CH2:32][CH2:33][N:34]1C(=O)C2C(=CC=CC=2)C1=O)[CH:19]1[C:28]2[N:27]=[C:26]([CH3:29])[CH:25]=[CH:24][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]=[C:26]([CH3:29])[CH:25]=[CH:24][C:23]=2[CH2:22][CH2:21][CH2:20]1)[CH2:30][CH2:31][CH2:32][CH2:33][NH2:34]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 69296760HCID 69296760, compound

Product 1

HCID 10286988HCID 10286988, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-{[[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-(2-methyl-5,6,7,8-tetrahydroquinolin-8-yl)-amino]-methyl}-benzoimidazole-1-carboxylic acid tert-butyl ester (228 mg, 0.384 mmol) in ethanol (10 mL) at room temperature was added hydrazine hydrate (0.10 mL). The mixture was stirred for 4 days. The mixture was concentrated in vaccuo and the resultant material was purified by column chromatography on silica gel (1:1:10 MeOH: NH4OH: CH2Cl2) to provide the product as a colourless oil (82 mg, 59%): 1H NMR (CDCl3) δ 1.25-1.45 (m, 4H), 1.60-1.70 (m, 1H), 1.81-1.93 (m, 1H), 1.97-2.04 (m, 1H), 2.10-2.18 (m, 1H), 2.46-2.56 (m, 3H), 2.62-2.82 (m, 6H), 3.95-3.99 (m, 1H), 4.00 (d, 1H, J=17.1 Hz), 4.09 (d, 1H, J=17.1 Hz), 6.98 (d, 1H, J=7.8 Hz), 7.15-7.21 (m, 2H), 7.30 (d, 1H, J=7.8 Hz), 7.57-7.60 (m, 2H).

Workup

  1. concentrationThe mixture was concentrated in vaccuo
  2. customthe resultant material was purified by column chromatography on silica gel (1:1:10 MeOH: NH4OH: CH2Cl2)

Sources & evidence

ORD record
ord-48754ae0eca6446ca16318c3dd2de8a6
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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