HCID 178473565, compound → HCID 123386190, compound

HRID 1509137Notes

Reaction equation

HRID 1509137 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:21][C:22]4[NH:27][C:26](=[N:28][NH:29][C:30](OCC)=[O:31])[CH2:25][O:24][C:23]=4[N:35]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CN(C=O)C.ClCCl>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1([C:13]2[CH:18]=[CH:17][C:16]([C:19]3[C:20]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)=[CH:21][C:22]4[N:27]5[C:30](=[O:31])[NH:29][N:28]=[C:26]5[CH2:25][O:24][C:23]=4[N:35]=3)=[CH:15][CH:14]=2)[CH2:12][CH2:11][CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 178473565HCID 178473565, compound

Product 1

HCID 123386190HCID 123386190, compoundYield 34.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Ethyl 2-(6-(4-(1-(tert-butoxycarbonylamino)cyclobutyl)phenyl)-7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2(3H)-ylidene)hydrazinecarboxylate (24 mg, 0.04 mmol) in dry DMF (1 mL) was heated at 200° C. for 10 min under microwave irradiation. The reaction mixture was diluted with dichloromethane, filtered on celite and concentrated to dryness under reduced pressure. The resulting residue was purified by preparative HPLC (method G, gradient 5 to 95% 0.1% FA/ACN in 0.1% FA/H2O) to give the title compound (7 mg, 32%). 1H NMR (500 MHz, CDCl3): 9.18 (1H, br s), 8.54 (1H, s), 7.32 (2H, d), 7.28-7.26 (5H,m), 7.22-7.20 (2H,m), 5.32 (2H, s), 5.07 (1H, br s), 2.55-2.25 (4H, m), 2.10-2.03 (1H, m), 1.86-1.78 (1H, m), 1.44-1.15 (9H, br).

Workup

  1. filtrationfiltered on celite and
  2. concentrationconcentrated to dryness under reduced pressure
  3. customThe resulting residue was purified by preparative HPLC (method G, gradient 5 to 95% 0.1% FA/ACN in 0.1% FA/H2O)

Sources & evidence

ORD record
ord-5c67a51b6c4048dab4de873ad17ebe22
Source dataset
uspto-grants-2015_12
Patent number
US09221838B2

Reaction notes

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