10-Bromo-9-fluoro-3-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide → 10-bromo-9-fluoro-3-(1H-pyrazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

HRID 575143Notes

Reaction equation

HRID 575143 reaction equation
[Br:1][C:2]1[C:3]([F:20])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12](I)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:19]=1.CC1(C)C(C)(C)OB([C:29]2[CH:33]=[CH:32][NH:31][N:30]=2)O1>>[Br:1][C:2]1[C:3]([F:20])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([C:29]4[CH:33]=[CH:32][NH:31][N:30]=4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:19]=1

Participants

3

Reactant 2

HCID 8669305210-Bromo-9-fluoro-3-iodo-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideHCID 178431094HCID 178431094, compound

Product 1

HCID 17851377810-bromo-9-fluoro-3-(1H-pyrazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide

Procedure

10-Bromo-9-fluoro-3-iodo-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide (0.2 g) was reacted with 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole similar to as described in Example 4 and triturated from water followed by methanol to give 107 mg of 10-bromo-9-fluoro-3-(1H-pyrazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide. This intermediate was reacted with 2-Methyl-3-butyne-ol similar to as described in Procedure E to afford 3.3 mg of 9-fluoro-10-(3-hydroxy-3-methyl-but-1-ynyl)-3-(1H-pyrazol-3-yl)-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide following reverse phase hplc purification. MS (Q1) 396 (M)+.

Workup

  1. customtriturated from water

Sources & evidence

ORD record
ord-cb83abd4fe3447e8abf46fc543886939
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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