Dimethylbarbituric acid → HCID 53372245, compound

HRID 340785Notes

Reaction equation

HRID 340785 reaction equation
[C:1]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:28]([Cl:29])=[CH:27][C:10]3[N:11](CC=C)[C:12]([O:14][CH2:15][CH:16]4[CH2:18][CH:17]4[C:19]([O:21]CC)=[O:20])=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.CN1C(=O)CC(=O)N(C)C1=O>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCO>[C:1]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:2]=[CH:3][C:4]([C:7]2[C:28]([Cl:29])=[CH:27][C:10]3[NH:11][C:12]([O:14][CH2:15][CH:16]4[CH2:18][CH:17]4[C:19]([OH:21])=[O:20])=[N:13][C:9]=3[CH:8]=2)=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 69860Dimethylbarbituric acidHCID 67410049HCID 67410049, compound

Product 1

HCID 53372245HCID 53372245, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolvent

Procedure

The title compound was prepared from ethyl 2-({[5-(biphenyl-4-yl)-6-chloro-1-(prop-2-en-1-yl)-1H-benzimidazol-2-yl]oxy}methyl)cyclopropanecarboxylate (115 mg, 0.236 mmol), 1,3-dimethylbarbituric acid (111 mg, 0.708 mmol), Pd(PPh3)4 (30 mg, 0.026 mmol) and EtOH (2.5 ml) according to the procedure described for Example 13, Step B. Purification of the resulting crude product by reverse phase HPLC eluting with 35-100% MeCN:water afforded the title compound as a white solid. LC-MS: calculated for C24H19ClN2O3 418.11, observed m/e: 418.97 (M+H)+ (Rt 2.12/4 min). 1H NMR (500 MHz, CD3OD): 7.75-7.35 (m, 11H), 4.50 (dd, 2H), 4.30 (dd, 2H) 1.85 (m, 1H), 1.70 (m, 1H), 1.10 (m, 11H), 1.05 (m, 1H).

Workup

  1. customPurification of the resulting crude product by reverse phase HPLC
  2. washeluting with 35-100% MeCN

Sources & evidence

ORD record
ord-1cdb52c1c19746d5892daeafd2ad3bf9
Source dataset
uspto-grants-2014_11
Patent number
US08895596B2

Reaction notes

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