O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamine → USRE47493, Example 72

HRID 517284Notes

Reaction equation

HRID 517284 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:11](=[O:30])[N:10]2[C:31]([NH:33][CH:34]2[CH2:39][CH2:38][S:37](=[O:40])[CH2:36][CH2:35]2)=[O:32])=[CH:5][CH:4]=1)#[N:2].C1(C)C=C(C)C=C(C)C=1S(O[NH2:53])(=O)=O>ClCCl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:18]3[C:17](=[O:19])[CH2:16][CH2:15][CH2:14][C:13]=3[N:12]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=3)[C:11](=[O:30])[N:10]2[C:31]([NH:33][CH:34]2[CH2:39][CH2:38][S:37](=[NH:53])(=[O:40])[CH2:36][CH2:35]2)=[O:32])=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 2

HCID 11830845O-(2,4,6-Trimethylbenzenesulfonyl)hydroxylamineHCID 86732410USRE47493, Example 71

Product 1

HCID 86732411USRE47493, Example 72

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-(4-Cyanophenyl)-2,5-dioxo-N-(1-oxo-hexahydro-1λ4-thiopyran-4-yl)-1-(3-(trifluoromethyl)phenyl)-1,2,5,6,7,8-hexahydroquinazoline-3(4H)-carboxamide (example 71, 67 mg, 0.12 mmol) is added to a solution of O-mesitylenesulfonylhydroxylamine (25 mg, 0.12 mmol) in dichloromethane (1.0 mL), and the mixture is stirred at room temperature over night. All volatiles are removed under reduced pressure, and the residue is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 18 mg; ESI mass spectrum [M+H]+=586; Retention time HPLC: 0.92 min (Z018_S04).

Workup

  1. customAll volatiles are removed under reduced pressure
  2. customthe residue is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  3. custom0.92 min (Z018_S04)

Sources & evidence

ORD record
ord-dae0061d62ff419092ec0cfbb5d06727
Source dataset
uspto-grants-2015_08
Patent number
US09115093B2

Reaction notes

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