tert-Butyl bromoacetate → Methyl 4-(1-(2-tert-butoxy-2-oxoethyl)-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate

HRID 528999Notes

Reaction equation

HRID 528999 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].[C:39]([O:43][C:44](=[O:47])[CH2:45]Br)([CH3:42])([CH3:41])[CH3:40]>>[C:39]([O:43][C:44](=[O:47])[CH2:45][N:11]1[CH:12]=[C:8]([C:6](=[O:7])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:35][CH2:36][CH2:37][CH3:38])[N:9]=[C:10]1[C:13]1[CH:22]=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[C:23]([N:25]1[CH2:34][CH2:33][C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:26]1)=[O:24])([CH3:42])([CH3:41])[CH3:40]

Participants

3

Reactant 2

HCID 79177tert-Butyl bromoacetateHCID 178449064HCID 178449064, compound

Product 1

HCID 71062593Methyl 4-(1-(2-tert-butoxy-2-oxoethyl)-4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoateYield 90%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 264K, methyl 4-(4-(dibutylcarbamoyl)-1H-imidazol-2-yl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (310 mg, 0.6 mmol) and t-butylbromoacetate (117 mg, 0.6 mmol) were converted to the title compound (300 mg, 90%). MS(ESI+) m/z 631.4 (M+H)+.

Sources & evidence

ORD record
ord-1a1af3098721458eb411c42c2dc43953
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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