(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-carbamic acid t-butyl ester → CXCR4 antagonist 1

HRID 2080712Notes

Reaction equation

HRID 2080712 reaction equation
C(OC(=O)[N:7]([CH2:30][CH2:31][CH2:32][CH2:33][N:34]([CH2:38][CH2:39][CH3:40])[CH2:35][CH2:36][CH3:37])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][N:16]([CH2:24][C:25]2[NH:26][CH:27]=[CH:28][N:29]=2)[CH2:17][C:18]2[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=2)=[CH:11][CH:10]=1)(C)(C)C.Cl.CO>CO>[NH:29]1[CH:28]=[CH:27][N:26]=[C:25]1[CH2:24][N:16]([CH2:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][NH:7][CH2:30][CH2:31][CH2:32][CH2:33][N:34]([CH2:35][CH2:36][CH3:37])[CH2:38][CH2:39][CH3:40])=[CH:10][CH:11]=1)[CH2:17][C:18]1[N:19]([CH3:23])[CH:20]=[CH:21][N:22]=1

Participants

4

Reactant 2

HCID 11592205(4-dipropylamino-butyl)-(4-[[(1H-imidazol-2-ylmethyl)-(1-methyl-1H-imidazol-2-ylmethyl)-amino]-methyl]-benzyl)-carbamic acid t-butyl esterHCID 21893726Hydrochloride methanol

Product 1

HCID 58801930CXCR4 antagonist 1Yield 98.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (197 mg) obtained in Example 1-7 was dissolved in methanol (1.0 ml) and added with a 10% hydrogen chloride/methanol solution (3.0 ml) and the whole was stirred overnight at room temperature. After completion of the reaction, the solvent was distilled off and a hydrochloride (159 mg) of the subject compound was obtained as a white solid.

Workup

  1. customAfter completion of the reaction
  2. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-58856b9028d84a10ad8458e113a9ff31
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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