4-Methylmorpholine → 2-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic acid (4,4-dimethyl-cyclohexyl)-amide

HRID 1406503Notes

Reaction equation

HRID 1406503 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[N:14](C)[C:13]2[CH:16]=[C:17]([C:20](O)=[O:21])[CH:18]=[CH:19][C:12]=2[N:11]=1.Cl.[CH3:24][C:25]1([CH3:32])[CH2:30][CH2:29][CH:28]([NH2:31])[CH2:27][CH2:26]1.[CH3:33]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CN1CCOCC1>CN(C=O)C>[CH3:24][C:25]1([CH3:32])[CH2:30][CH2:29][CH:28]([NH:31][C:20]([C:17]2[CH:18]=[CH:19][C:12]3[N:11]([CH3:33])[C:10]([NH:9][C:3]4[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=4[Cl:8])=[N:14][C:13]=3[CH:16]=2)=[O:21])[CH2:27][CH2:26]1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 241919284,4-Dimethylcyclohexanamine hydrochlorideHCID 685192872-(2,6-dichloro-phenylamino)-1-methyl-1H-benzimidazole-6-carboxylic acid

Product 1

HCID 585623002-(2,6-Dichloro-phenylamino)-1-methyl-1H-benzimidazole-5-carboxylic acid (4,4-dimethyl-cyclohexyl)-amide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Prepared analogously to example 3c from 2-(2,6-dichloro-phenylamino)-1-methyl-1H-benzimidazole-6-carboxylic acid, 4,4-dimethyl-cyclohexylamine hydrochloride, TBTU and NMM in DMF; mp: 189-190° C., Rf value: 0.56 (silica gel; petrol ether/ethyl acetate=2:1).

Sources & evidence

ORD record
ord-4199d8d406f14029be7940b71db40fda
Source dataset
uspto-grants-2014_12
Patent number
US08916599B2

Reaction notes

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