(2-Methoxyethyl)(methyl)amine → HCID 89754896, compound

HRID 575324Notes

Reaction equation

HRID 575324 reaction equation
[Br:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[CH:11]3[CH2:12][CH:9]([CH2:10]3)[N:8]3[C:13]([CH:19]=O)=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:21]=1.[CH3:23][O:24][CH2:25][CH2:26][NH:27][CH3:28]>>[Br:1][C:2]1[C:3]([F:22])=[CH:4][C:5]2[CH:11]3[CH2:10][CH:9]([CH2:12]3)[N:8]3[C:13]([CH2:19][N:27]([CH2:26][CH2:25][O:24][CH3:23])[CH3:28])=[C:14]([C:16]([NH2:18])=[O:17])[N:15]=[C:7]3[C:6]=2[CH:21]=1

Participants

3

Reactant 2

HCID 300977(2-Methoxyethyl)(methyl)amineHCID 8669316110-bromo-9-fluoro-3-formyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide

Product 1

HCID 89754896HCID 89754896, compound

Procedure

10-bromo-9-fluoro-3-formyl-6,7-dihydro-5H-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide (75 mg) was reacted with N-(methoxyethyl)methylamine similarly to as described in the synthesis of 9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-3-[(4-methylpiperazin-1-yl)methyl]-5,6,7,12-tetrahydro-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide to afford 10-bromo-9-fluoro-3-(((2-methoxyethyl)(methyl)amino)methyl)-6,7-dihydro-5H-5,7-methanobenzo [c]imidazo[1,2-a]azepine-2-carboxamide which was directly reacted with 2-Methyl-3-butyne-ol via General Procedure E to afford 24 mg (26%) of 9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-3-[[2-methoxyethyl(methyl)amino]methyl]-5,6,7,12-tetrahydro-5,7-methanobenzo[c]imidazo[1,2-a]azepine-2-carboxamide. M+1=441.

Sources & evidence

ORD record
ord-ea44848f210341929c9a489cbc5062a1
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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