Cyclopropylamine → (+/-)-9-(3-Cyclopropylcarbamoyl-3-hydroxy-but-1-ynyl)-8-fluoro-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid amide

HRID 575234Notes

Reaction equation

HRID 575234 reaction equation
[C:1]([C:4]1[N:5]=[C:6]2[C:12]3[CH:13]=[C:14]([C:18]#[C:19][C:20]([OH:26])([CH3:25])[C:21](OC)=[O:22])[C:15]([F:17])=[CH:16][C:11]=3[O:10][CH2:9][CH2:8][N:7]2[CH:27]=1)(=[O:3])[NH2:2].[CH:28]1([NH2:31])[CH2:30][CH2:29]1>CO>[CH:28]1([NH:31][C:21](=[O:22])[C:20]([OH:26])([CH3:25])[C:19]#[C:18][C:14]2[C:15]([F:17])=[CH:16][C:11]3[O:10][CH2:9][CH2:8][N:7]4[CH:27]=[C:4]([C:1]([NH2:2])=[O:3])[N:5]=[C:6]4[C:12]=3[CH:13]=2)[CH2:30][CH2:29]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 86693109Methyl 4-(2-carbamoyl-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-10-yl)-2-hydroxy-2-methylbut-3-ynoate

Product 1

HCID 86693111(+/-)-9-(3-Cyclopropylcarbamoyl-3-hydroxy-but-1-ynyl)-8-fluoro-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulene-2-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl 4-(2-carbamoyl-9-fluoro-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepin-10-yl)-2-hydroxy-2-methylbut-3-ynoate (120 mg, 0.32 mmol, 1.00 equiv) and cyclopropanamine (1.83 g, 32.05 mmol, 99.72 equiv) in methanol (2 mL) was stirred for 12 h at 40° C. The resulting mixture was concentrated under vacuum and the residue was applied onto a silica gel column with dichloromethane/methanol (30:1) to give the titled compound, 23 mg (18%), as a yellow solid.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-9bae879cb10c4948b34787f0b7900246
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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