(S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline → Methyl 3-((S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(4-(dibutylcarbamoyl)-1-(3-(4-methylpiperazin-1-yl)propyl)-1H-imidazol-2-yl)benzoate

HRID 529023Notes

Reaction equation

HRID 529023 reaction equation
[CH2:1]([N:5]([CH2:36][CH2:37][CH2:38][CH3:39])[C:6]([C:8]1[N:9]=[C:10]([C:23]2[CH:31]=[CH:30][C:29]([C:32]([O:34][CH3:35])=[O:33])=[CH:28][C:24]=2[C:25]([OH:27])=O)[N:11]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[Si:40]([O:47][CH2:48][C@@H:49]1[CH2:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH2:51][NH:50]1)([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41]>>[Si:40]([O:47][CH2:48][C@@H:49]1[CH2:58][C:57]2[C:52](=[CH:53][CH:54]=[CH:55][CH:56]=2)[CH2:51][N:50]1[C:25]([C:24]1[CH:28]=[C:29]([CH:30]=[CH:31][C:23]=1[C:10]1[N:11]([CH2:13][CH2:14][CH2:15][N:16]2[CH2:21][CH2:20][N:19]([CH3:22])[CH2:18][CH2:17]2)[CH:12]=[C:8]([C:6](=[O:7])[N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH2:36][CH2:37][CH2:38][CH3:39])[N:9]=1)[C:32]([O:34][CH3:35])=[O:33])=[O:27])([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41]

Participants

3

Reactant 2

HCID 10333747(S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinolineHCID 710608872-(4-(dibutylcarbamoyl)-1-(3-(4-methylpiperazin-1-yl)propyl)-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acid

Product 1

HCID 86718941Methyl 3-((S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(4-(dibutylcarbamoyl)-1-(3-(4-methylpiperazin-1-yl)propyl)-1H-imidazol-2-yl)benzoateYield 93.6%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 271H, 2-(4-(dibutylcarbamoyl)-1-(3-(4-methylpiperazin-1-yl)propyl)-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acid (110 mg, 0.2 mmol) and (S)-3-((tert-butyldimethylsilyloxy)methyl)-1,2,3,4-tetrahydroisoquinoline (73 mg, 0.26 mmol) were converted to the title compound (150 mg, 93%). MS(ESI+) m/z 802.4 (M+H)+.

Sources & evidence

ORD record
ord-bc27c585d3dc452ca26e258b40c31d27
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

Loading…