Diisopropylethylamine → N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methoxy-propyl]-3-methyl-4-(morpholin-3-on-4-yl)-benzamide

HRID 1629862Notes

Reaction equation

HRID 1629862 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][C:12]1=[O:17])[C:5]([OH:7])=O.[Cl:18][C:19]1[CH:33]=[CH:32][C:22]2[NH:23][C:24]([C@@H:26]([NH2:31])[CH2:27][CH2:28][O:29][CH3:30])=[N:25][C:21]=2[CH:20]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>C1COCC1>[Cl:18][C:19]1[CH:33]=[CH:32][C:22]2[NH:23][C:24]([C@@H:26]([NH:31][C:5](=[O:7])[C:4]3[CH:8]=[CH:9][C:10]([N:11]4[CH2:16][CH2:15][O:14][CH2:13][C:12]4=[O:17])=[C:2]([CH3:1])[CH:3]=3)[CH2:27][CH2:28][O:29][CH3:30])=[N:25][C:21]=2[CH:20]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 670485263-Methyl-4-(3-oxomorpholin-4-yl)benzoic acidHCID 178495121(S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methoxypropylamine

Product 1

HCID 178495123N-[(1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methoxy-propyl]-3-methyl-4-(morpholin-3-on-4-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Prepared analogously to Example 1f from 3-methyl-4-(morpholin-3-on-4-yl)-benzoic acid, (1S)-1-(5-chloro-1H-benzimidazol-2-yl)-3-methoxy-propylamine, TBTU and DIPEA in THF with subsequent purification by chromatography on silica gel.

Sources & evidence

ORD record
ord-33812b0ebeaf4feebe4629ef4f34e845
Source dataset
uspto-grants-2014_07
Patent number
US08791103B2

Reaction notes

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