Diisopropylamine → HCID 178467680, compound

HRID 575397Notes

Reaction equation

HRID 575397 reaction equation
Br[C:2]1[C:3]([F:27])=[CH:4][C:5]2[O:11][CH2:10][CH2:9][N:8]3[C:12]([C:18]4[NH:22][N:21]=[C:20]([CH:23]5[CH2:25][CH2:24]5)[N:19]=4)=[C:13]([C:15]([NH2:17])=[O:16])[N:14]=[C:7]3[C:6]=2[CH:26]=1.[CH3:28][C:29]([OH:34])([C:32]#[CH:33])[CH2:30][OH:31].C(NC(C)C)(C)C>CN(C=O)C>[CH:23]1([C:20]2[N:19]=[C:18]([C:12]3[N:8]4[CH2:9][CH2:10][O:11][C:5]5[CH:4]=[C:3]([F:27])[C:2]([C:33]#[C:32][C:29]([OH:34])([CH3:28])[CH2:30][OH:31])=[CH:26][C:6]=5[C:7]4=[N:14][C:13]=3[C:15]([NH2:17])=[O:16])[NH:22][N:21]=2)[CH2:25][CH2:24]1

Participants

5

Reactant 3

HCID 7912DiisopropylamineHCID 221369052-Methylbut-3-yne-1,2-diolHCID 178513780HCID 178513780, compound

Product 1

HCID 178467680HCID 178467680, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3-cyclopropyl-1H-1,2,4-triazol-5-yl)-10-(3,4-dihydroxy-3-methyl-but-1-ynyl)-9-fluoro-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was prepared similarly according to General Procedure E with slight modification. 10-bromo-3-(3-cyclopropyl-1H-1,2,4-triazol-5-yl)-9-fluoro-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was reacted with 2-methylbut-3-yne-1,2-diol in a solution of DMF (1.3 mL/mmol) and diisopropylamine (2.6 mL/mmol) to afford 30 mg of the titled compound (47.1% yield). M+1=453.0.

Workup

  1. custom3-(3-cyclopropyl-1H-1,2,4-triazol-5-yl)-10-(3,4-dihydroxy-3-methyl-but-1-ynyl)-9-fluoro-5,6-dihydroimidazo[1,2-d][1,4]benzoxazepine-2-carboxamide was prepared similarly

Sources & evidence

ORD record
ord-450ccafba2104552ba6c1fba24d75f31
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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