Hydrogen chloride-ethyl acetate → 10-((3-Hydroxypyrrolidin-3-yl)ethynyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamide

HRID 575073Notes

Reaction equation

HRID 575073 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C:10]([C:14]#[C:15][C:16]2[CH:17]=[CH:18][C:19]3[O:28][CH2:27][CH2:26][N:25]4[C:21](=[N:22][C:23]([C:29](=[O:31])[NH2:30])=[CH:24]4)[C:20]=3[CH:32]=2)([OH:13])[CH2:9]1)=O)(C)(C)C.Cl.CC(=O)OCC>CO>[OH:13][C:10]1([C:14]#[C:15][C:16]2[CH:17]=[CH:18][C:19]3[O:28][CH2:27][CH2:26][N:25]4[CH:24]=[C:23]([C:29]([NH2:30])=[O:31])[N:22]=[C:21]4[C:20]=3[CH:32]=2)[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 866931003-(2-Carbamoyl-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-9-ylethynyl)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 8669310110-((3-Hydroxypyrrolidin-3-yl)ethynyl)-5,6-dihydrobenzo[f]imidazo[1,2-d][1,4]oxazepine-2-carboxamideYield 10.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a solution of 3-(2-Carbamoyl-4,5-dihydro-6-oxa-1,3a-diaza-benzo[e]azulen-9-ylethynyl)-3-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester (40 mg, 0.1 mmol) in methanol (20 ml) was added HCl/EA (20 ml). The solution was stirred for 3 h at room temperature. The reaction mixture was purified by column to afford the titled compound (3.5 mg, 10%). 1HNMR (Methanol-d4, 400 MHz): δ 8.62 (d, J=2.0 Hz, 1H), 7.78 (s, 1H), 7.41 (dd, J=2.0, 8.8 Hz, 1H), 7.08 (d, J=8.4 Hz, 1H), 4.52 (s, 4H), 3.54-3.40 (m, 4H), 2.43 (t, J=5.4 Hz, 2H), LCMS: 339.1 [M+H]+.

Workup

  1. customThe reaction mixture was purified by column

Sources & evidence

ORD record
ord-dc9f33b837e7430e9c3d100eabaea1f2
Source dataset
uspto-grants-2015_05
Patent number
US09034866B2

Reaction notes

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