Dicyclohexylcarbodiimide → HCID 178492570, compound

HRID 710536Notes

Reaction equation

HRID 710536 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][CH2:12][C:13](O)=O.C1CCC(N=C=NC2CCCCC2)CC1.[N:31]1[C:35]2[CH:36]=[CH:37][C:38]([C:40]([NH:42][NH2:43])=O)=[CH:39][C:34]=2[NH:33][CH:32]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:53])=CC=1>>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][CH2:12][C:13]1[S:53][C:40]([C:38]2[CH:37]=[CH:36][C:35]3[NH:31][CH:32]=[N:33][C:34]=3[CH:39]=2)=[N:42][N:43]=1

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 663432,5-Dimethoxyhydrocinnamic acidHCID 87949Lawesson's reagentHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178492570HCID 178492570, compound

Procedure

The compound was synthesized starting from 3-(2,5-dimethoxyphenyl)propionic acid (210 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: 0.04 g (10.9%); MS m/z: 367.3 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.03 (t, 2H, 3J=7.5 Hz); 3.38 (t, 2H, 3J=7.5 Hz); 3.66 (s, 3H); 3.73 (s, 3H); 6.76 (dd, 1H, 4J=2.9 Hz, 3J=9.1 Hz); 6.82 (d, 1H, 4J=2.9 Hz); 6.89 (d, 1H, 3J=9.1 Hz); 7.81 (d, 1H, 3J=8.7 Hz); 7.89 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 8.21 (d, 1H, 4J=1.7 Hz); 8.82 (s, 1H); HPLC (METHOD [A]): rt 12.62 min (93.1%)

Workup

  1. customThe compound was synthesized
  2. customrt 12.62 min (93.1%)

Sources & evidence

ORD record
ord-96dfce12e309404b8c557afcd118b088
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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