3-Bromo-N,N-dimethylpropan-1-amine → Methyl 4-(4-(dibutylcarbamoyl)-1-(3-(dimethylamino)propyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

HRID 529003Notes

Reaction equation

HRID 529003 reaction equation
[CH2:1]([N:5]([CH2:35][CH2:36][CH2:37][CH3:38])[C:6]([C:8]1[N:9]=[C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])[NH:11][CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].Br[CH2:40][CH2:41][CH2:42][N:43]([CH3:45])[CH3:44]>>[CH2:35]([N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:6]([C:8]1[N:9]=[C:10]([C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=2[C:23]([N:25]2[CH2:34][CH2:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:26]2)=[O:24])[N:11]([CH2:40][CH2:41][CH2:42][N:43]([CH3:45])[CH3:44])[CH:12]=1)=[O:7])[CH2:36][CH2:37][CH3:38]

Participants

3

Reactant 2

HCID 124407753-Bromo-N,N-dimethylpropan-1-amineHCID 178449064HCID 178449064, compound

Product 1

HCID 71062235Methyl 4-(4-(dibutylcarbamoyl)-1-(3-(dimethylamino)propyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoateYield 78.7%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 266A, methyl 4-(4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (200 mg, 0.38 mmol) and 3-bromo-N,N-dimethylpropan-1-amine (77 mg, 0.46 mmol) were converted to the title compound (180 mg, 78%). MS(ESI+) m/z 602.6 (M+H)+.

Sources & evidence

ORD record
ord-bf4a775bf2c24e618495888338b98fc2
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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