Phenyl isocyanate → HCID 58577872, compound

HRID 473958Notes

Reaction equation

HRID 473958 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:10]1[CH2:15][CH2:14][NH:13][C:12]2[CH:16]=[CH:17][C:18]([C:20]3[CH:21]=[CH:22][C:23]([O:26][CH2:27][C:28]([CH3:34])([CH3:33])[C:29]([O:31][CH3:32])=[O:30])=[N:24][CH:25]=3)=[CH:19][C:11]1=2>C(Cl)Cl>[CH3:33][C:28]([CH3:34])([CH2:27][O:26][C:23]1[CH:22]=[CH:21][C:20]([C:18]2[CH:17]=[CH:16][C:12]3[N:13]([C:8](=[O:9])[NH:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:14][CH2:15][O:10][C:11]=3[CH:19]=2)=[CH:25][N:24]=1)[C:29]([O:31][CH3:32])=[O:30]

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 58577812HCID 58577812, compound

Product 1

HCID 58577872HCID 58577872, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Phenyl isocyanate (16.1 μL, 0.148 mmol) was added at room temperature to a solution of methyl 3-(5-(3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)pyridin-2-yloxy)-2,2-dimethylpropanoate B-2 (39.2 mg, 0.114 mmol) in anhydrous methylene chloride (0.57 mL) under an atmosphere of argon. The reaction mixture was stirred overnight, then concentrated to dryness under reduced pressure to give crude methyl 2,2-dimethyl-3-(5-(4-(phenylcarbamoyl)-3,4-dihydro-2H-benzo[b][1,4]oxazin-7-yl)pyridin-2-yloxy)propanoate B-3 (62.0 mg), which was sufficiently pure to be used for the next step without additional purification. MS (ESI), [M+1]+ 462.

Workup

  1. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-7c3ba08ac18a43c8862fe9c14d940c4d
Source dataset
uspto-grants-2014_01
Patent number
US08637507B2

Reaction notes

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