Water → Methyl 2-carbamoyl-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-3-carboxylate

HRID 575150Notes

Reaction equation

Br[C:2]1[C:3]([F:23])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([C:18]([O:20][CH3:21])=[O:19])=[C:13]([C:15](=[O:17])[NH2:16])[N:14]=[C:7]3[C:6]=2[CH:22]=1.[CH3:24][CH:25]([C:28]#[CH:29])[CH2:26]O.[OH2:30]>>[C:15]([C:13]1[N:14]=[C:7]2[C:6]3[CH:22]=[C:2]([C:29]#[C:28][C:25]([OH:30])([CH3:26])[CH3:24])[C:3]([F:23])=[CH:4][C:5]=3[O:11][CH2:10][CH2:9][N:8]2[C:12]=1[C:18]([O:20][CH3:21])=[O:19])(=[O:17])[NH2:16]

Participants

Reactant 3

HCID 962Water

HCID 1024422-Methylbut-3-yn-1-ol

HCID 86693166Methyl 10-bromo-2-carbamoyl-9-fluoro-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-3-carboxylate

Product 1

HCID 86693170Methyl 2-carbamoyl-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-3-carboxylate

Procedure

Methyl 10-bromo-2-carbamoyl-9-fluoro-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-3-carboxylate (2 g) was reacted with 2-Methyl-3-butyne-ol similar to as described in Procedure E to afford 2 g of methyl 2-carbamoyl-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-3-carboxylate following triteration from water. MS (Q1) 388 (M)+. Methyl 2-carbamoyl-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-3-carboxylate (1.5 g) was saponified with LiOH in water/THF to afford quantitative yield of 2-carbamoyl-9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-3-carboxylic acid. MS (Q1) 383 (M)+.

Sources & evidence

ORD record: ord-b54fc1552f1d41cda1d58a5f96119818
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09034866B2

Reaction notes

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