N,N-Dimethyl-1,3-propanediamine → 4-(3-Dimethylaminopropylcarbamoyl)-2-fluoro-1-triphenylmethylimidazole

HRID 2412510Notes

Reaction equation

HRID 2412510 reaction equation
[F:1][C:2]1[N:3]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:4]=[C:5]([C:7](O)=[O:8])[N:6]=1.[CH3:29][N:30]([CH3:35])[CH2:31][CH2:32][CH2:33][NH2:34]>C1COCC1>[CH3:29][N:30]([CH3:35])[CH2:31][CH2:32][CH2:33][NH:34][C:7]([C:5]1[N:6]=[C:2]([F:1])[N:3]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:4]=1)=[O:8]

Participants

4

Reactant 2

HCID 7993N,N-Dimethyl-1,3-propanediamineHCID 204324044-Carboxy-2-fluoro-1-triphenylmethylimidazole

Product 1

HCID 204324414-(3-Dimethylaminopropylcarbamoyl)-2-fluoro-1-triphenylmethylimidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-Fluoro-1-triphenylmethylimidazole-4-carboxylic acid and 3-dimethylaminopropylamine were condensed in THF by the mixed anhydride procedure described for the preparation of starting material for Example 18, to give 4-(3-dimethylaminopropylcarbamoyl)-2-fluoro-1-triphenylmethylimidazole, having the following n.m.r. in CDCl3 : 1.8 (m, 2H); 2.3 (s, 6H); 2.4 (t, 2H); 3.5 (q, 2H); 7.0-7.6 (m, 16H).

Workup

  1. customdescribed for the preparation of starting material for Example 18

Sources & evidence

ORD record
ord-a7828a0d66464e6da3cacdfc8727b6ff
Source dataset
uspto-grants-1985_01
Patent number
US04492692

Reaction notes

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