Dicyclohexylcarbodiimide → HCID 178489913, compound

HRID 710530Notes

Reaction equation

HRID 710530 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][CH2:14][C:15](O)=O)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C1CCC(N=C=NC2CCCCC2)CC1.[N:33]1[C:37]2[CH:38]=[CH:39][C:40]([C:42]([NH:44][NH2:45])=O)=[CH:41][C:36]=2[NH:35][CH:34]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:55])=CC=1>>[CH3:12][O:11][C:7]1[CH:6]=[C:5]([CH:4]=[C:3]([O:2][CH3:1])[C:8]=1[O:9][CH3:10])[CH2:13][CH2:14][C:15]1[S:55][C:42]([C:40]2[CH:39]=[CH:38][C:37]3[NH:33][CH:34]=[N:35][C:36]=3[CH:41]=2)=[N:44][N:45]=1

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 648603,4,5-Trimethoxyhydrocinnamic acidHCID 87949Lawesson's reagentHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178489913HCID 178489913, compound

Procedure

The compound was synthesized starting from 3-(3,4,5-trimethoxyphenyl)propionic acid (241 mg; 1 mmol), DCC (206 mg; 1 mmol), benzimidazol-5-carbohydrazide (176 mg; 1 mmol) and Lawesson's reagent (606 mg; 1.5 mmol) as described in method 2; yield: 0.033 g (8.3%); MS m/z: 397.3 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.04 (t, 2H, 3J=7.9 Hz); 3.47 (t, 2H, 3J=7.9 Hz); 3.62 (s, 3H); 3.74 (s, 6H); 6.62 (s, 2H); 7.83 (d, 1H, 3J=8.7 Hz); 7.93 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 8.22 (d, 1H, 4J=1.7 Hz); 8.91 (s, 1H); HPLC (METHOD [A]): rt 11.54 min (98.2%)

Workup

  1. customThe compound was synthesized
  2. customrt 11.54 min (98.2%)

Sources & evidence

ORD record
ord-4496f7eecd0643d0b5a4650b3f3b4c7b
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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