Dicyclohexylcarbodiimide → HCID 178490025, compound

HRID 710528Notes

Reaction equation

HRID 710528 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][C:12](O)=O)[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].C1CCC(N=C=NC2CCCCC2)CC1.[N:30]1[C:34]2[CH:35]=[CH:36][C:37]([C:39]([NH:41][NH2:42])=O)=[CH:38][C:33]=2[NH:32][CH:31]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:52])=CC=1>>[Cl:1][C:2]1[CH:3]=[C:4]([CH:5]=[CH:6][C:7]=1[O:8][CH3:9])[CH2:10][CH2:11][C:12]1[S:52][C:39]([C:37]2[CH:36]=[CH:35][C:34]3[NH:30][CH:31]=[N:32][C:33]=3[CH:38]=2)=[N:41][N:42]=1

Participants

5

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 87949Lawesson's reagentHCID 108892723-(3-chloro-4-methoxyphenyl)propanoic acidHCID 166371191H-benzimidazole-5-carbohydrazide

Product 1

HCID 178490025HCID 178490025, compound

Procedure

The compound was synthesized starting from 3-(3-chloro-4-methoxyphenyl)propionic acid (215 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: 0.032 g (8.6%); MS m/z: 371.1/373.2 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 3.05 (t, 2H, 3J=7.5 Hz); 3.44 (t, 2H, 3J=7.5 Hz); 3.81 (s, 3H); 7.05 (d, 1H, 3J=8.7 Hz); 7.22 (dd, 1H, 4J=2.1 Hz, 3J=8.7 Hz); 7.39 (d, 1H, 4J=2.1 Hz); 7.83 (d, 1H, 3J=8.7 Hz); 7.92 (dd, 1H, 4J=1.7 Hz, 3J=8.7 Hz); 8.22 (d, 1H, 4J=1.7 Hz); 8.93 (s, 1H); HPLC (METHOD [A]): rt 13.65 min (98.9%)

Workup

  1. customThe compound was synthesized
  2. customrt 13.65 min (98.9%)

Sources & evidence

ORD record
ord-17420c33bd9f41c1861c9427e041c68f
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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