(E)-2-chloropropyl 2-oxo-7-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-1-yl)prop-1-enyl)-2,3-dihydro-1H-pyrido[2,3-e][1,4]diazepine-4(5H)-carboxylate → (E)-7-(3-Oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-1-yl)prop-1-enyl)-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-one

HRID 83014Notes

Reaction equation

HRID 83014 reaction equation
[O:1]=[C:2]1[NH:8][C:7]2[N:9]=[CH:10][C:11](/[CH:13]=[CH:14]/[C:15](=[O:27])[N:16]3[CH2:19][CH:18]([O:20][CH2:21][C:22]4[S:23][CH:24]=[CH:25][CH:26]=4)[CH2:17]3)=[CH:12][C:6]=2[CH2:5][N:4](C(OCC(Cl)C)=O)[CH2:3]1>CO>[O:27]=[C:15]([N:16]1[CH2:19][CH:18]([O:20][CH2:21][C:22]2[S:23][CH:24]=[CH:25][CH:26]=2)[CH2:17]1)/[CH:14]=[CH:13]/[C:11]1[CH:10]=[N:9][C:7]2[NH:8][C:2](=[O:1])[CH2:3][NH:4][CH2:5][C:6]=2[CH:12]=1

Participants

3

Reactant 1

HCID 67154724(E)-2-chloropropyl 2-oxo-7-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-1-yl)prop-1-enyl)-2,3-dihydro-1H-pyrido[2,3-e][1,4]diazepine-4(5H)-carboxylate

Product 1

HCID 52950663(E)-7-(3-Oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-1-yl)prop-1-enyl)-4,5-dihydro-1H-pyrido[2,3-e][1,4]diazepin-2(3H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (E)-2-chloropropyl 2-oxo-7-(3-oxo-3-(3-(thiophen-2-ylmethoxy)azetidin-1-yl)prop-1-enyl)-2,3-dihydro-1H-pyrido[2,3-e][1,4]diazepine-4(5H)-carboxylate (75 mg, 0.15 mmol) in methanol (3 mL) was refluxed for 2 hours. After concentration to dryness, the residue was triturated in methanol. The title product was obtained as a white solid (75 mg, 19%).

Workup

  1. concentrationAfter concentration to dryness
  2. customthe residue was triturated in methanol

Sources & evidence

ORD record
ord-b09bd9a12fcf484cac5da698969fafd6
Source dataset
uspto-grants-2014_09
Patent number
US08846711B2

Reaction notes

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