Tetrahydrofuran → 4-Nitrophenyl 7-(6,7-dimethoxyquinolin-4-yloxy)-2,3-dihydrobenzo[b][1,4]oxazine-4-carboxylate

HRID 1925355Notes

Reaction equation

HRID 1925355 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]2[NH:24][CH2:23][CH2:22][O:21][C:20]=2[CH:25]=1.Cl[C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=1)=[O:28].C1COCC1>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[CH:18][C:19]2[N:24]([C:27]([O:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)=[O:28])[CH2:23][CH2:22][O:21][C:20]=2[CH:25]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 821294-Nitrophenyl chloroformateHCID 248240487-(6,7-dimethoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine

Product 1

HCID 675205844-Nitrophenyl 7-(6,7-dimethoxyquinolin-4-yloxy)-2,3-dihydrobenzo[b][1,4]oxazine-4-carboxylate

Procedure

To a solution of 7-(6,7-dimethoxyquinolin-4-yloxy)-3,4-dihydro-2H-benzo[b][1,4]oxazine (400 mg, 1.182 mmol) and p-nitrophenyl chloroformate (262 mg, 1.300 mmol) in THF (6 mL) DIPEA (245 μL, 1.419 mmol) was added drop wise at RT. The solution was stirred for 1 h at RT before the resulting mixture was concentrated in vacuo and the title compound was used in the following reaction without purification. MS (ESI, pos. ion) m/z: 504 (M+1). Mass cal'd for C26H21N3O8: 503.13.

Workup

  1. concentrationwas concentrated in vacuo
  2. customthe title compound was used in the following reaction without purification

Sources & evidence

ORD record
ord-92ac844f39eb410bb9421d4a8064f3fd
Source dataset
uspto-grants-2012_05
Patent number
US08178557B2

Reaction notes

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