2-(4-(Dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acid → Methyl 3-((S)-3-(azidomethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)benzoate

HRID 529027Notes

Reaction equation

HRID 529027 reaction equation
[CH2:1]([N:5]([CH2:27][CH2:28][CH2:29][CH3:30])[C:6]([C:8]1[N:9]=[C:10]([C:14]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][C:15]=2[C:16](O)=[O:17])[N:11]([CH3:13])[CH:12]=1)=[O:7])[CH2:2][CH2:3][CH3:4].[N:31]([CH2:34][C@@H:35]1[CH2:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37][NH:36]1)=[N+:32]=[N-:33]>>[N:31]([CH2:34][C@@H:35]1[CH2:44][C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH2:37][N:36]1[C:16]([C:15]1[CH:19]=[C:20]([CH:21]=[CH:22][C:14]=1[C:10]1[N:11]([CH3:13])[CH:12]=[C:8]([C:6](=[O:7])[N:5]([CH2:27][CH2:28][CH2:29][CH3:30])[CH2:1][CH2:2][CH2:3][CH3:4])[N:9]=1)[C:23]([O:25][CH3:26])=[O:24])=[O:17])=[N+:32]=[N-:33]

Participants

3

Reactant 2

HCID 710622052-(4-(Dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acidHCID 86718892(S)-3-(Azidomethyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 71086334Methyl 3-((S)-3-(azidomethyl)-1,2,3,4-tetrahydroisoquinoline-2-carbonyl)-4-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)benzoateYield 91%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 271H, 2-(4-(dibutylcarbamoyl)-1-methyl-1H-imidazol-2-yl)-5-(methoxycarbonyl)benzoic acid (230 mg, 0.55 mmol) and (S)-3-(azidomethyl)-1,2,3,4-tetrahydroisoquinoline (135 mg, 0.72 mmol) were converted to the title compound (280 mg, 91%). MS(ESI+) m/z 586.2 (M+H)+.

Sources & evidence

ORD record
ord-e02a16481d3449639edac6ef56225db2
Source dataset
uspto-grants-2016_05
Patent number
US09346795B2

Reaction notes

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