Hydroxylamine → HCID 86692012, compound

HRID 1423268Notes

Reaction equation

HRID 1423268 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][S:8][C:9]1[N:18]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:17](=[O:26])[C:16]2[C:11](=[CH:12][C:13]([C:27]#[N:28])=[CH:14][CH:15]=2)[N:10]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:30][OH:31]>C(O)(=O)C.N#N.CCOC(C)=O>[F:25][C:22]1[CH:23]=[CH:24][C:19]([N:18]2[C:17](=[O:26])[C:16]3[C:11](=[CH:12][C:13]([C:27](=[N:30][OH:31])[NH2:28])=[CH:14][CH:15]=3)[N:10]=[C:9]2[S:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:29])=[CH:20][CH:21]=1

Participants

6

Reactant 2

HCID 787HydroxylamineHCID 68277914HCID 68277914, compound

Product 1

HCID 86692012HCID 86692012, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 947NitrogenSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl-2-(7-cyano-3-(4-fluorophenyl)-4-oxo-3,4-dihydroquinazolin-2-ylthio)acetate (10A, 0.05 g, 0.12 mmol) in 50% NH2OH aqueous solution (3 mL) and 20 μL acetic acid was microwaved under high absorption in N2 atmosphere 105° C. for 40 minutes. The reaction was diluted with EtOAc and washed with water. The organic was concentrated to yield tert-butyl 2-(3-(4-fluorophenyl)-7-(N′-hydroxycarbamimidoyl)-4-oxo-3,4-dihydroquinazolin-2-ylthio)acetate (10B), MS (M+H)=445.

Workup

  1. washwashed with water
  2. concentrationThe organic was concentrated

Sources & evidence

ORD record
ord-b5fa4c2ece884a1f8d42239a6c8f97ca
Source dataset
uspto-grants-2015_01
Patent number
US08927559B2

Reaction notes

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