Pyridine → HCID 72340372, compound

HRID 1691462Notes

Reaction equation

HRID 1691462 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25](=O)[CH3:26])[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:28]=[C:29]([C:32]([F:35])([F:34])[F:33])[CH:30]=[CH:31][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.[NH2:37][OH:38].N1C=CC=CC=1>C(O)C>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([N:14]2[C:20]3[CH:21]=[C:22]([C:25](=[N:37][OH:38])[CH3:26])[CH:23]=[CH:24][C:19]=3[NH:18][C:17]3[N:28]=[C:29]([C:32]([F:35])([F:34])[F:33])[CH:30]=[CH:31][C:16]=3[CH2:15]2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 59618815HCID 59618815, compound

Product 1

HCID 72340372HCID 72340372, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 1-[6-[(4-tert-butylphenyl)sulfonyl]-2-(trifluoromethyl)-6,11-dihydro-5H-pyrido[2,3-b][1,5]benzodiazepin-8-yl]ethanone (Example 454, 19 mg, 0.0378 mmol), hydroxylamine hydrochloride (2.9 mg, 0.042 mmol), pyridine (0.15 mL), and ethanol (0.15 mL) was heated in a microwave reactor at 160° C. for 10 min. The volatiles were removed, and the residue was triturated with hexane/DCM. The solid was collected and dried to provide the title compound. LC/MS: m/e 504.0 (M+H)+. 1H NMR (500 MHz, acetone-d6): δ 8.88 (1H, s), 8.45 (1H, s), 7.78 (1H, s), 7.73 (1H, d, J=7.5 Hz), 7.64 (1H, d, J=8.5 Hz), 7.27 (1H, d, J=8.4 Hz), 7.20 (2H, d, J=8.0 Hz), 7.14 (1H, d, J=7.3 Hz), 6.97 (2H, d, J=7.8 Hz), 4.70-4.95 (2H, br), 2.05 (3H, s), 1.23 (9H, s).

Workup

  1. customThe volatiles were removed
  2. customthe residue was triturated with hexane/DCM
  3. customThe solid was collected
  4. customdried

Sources & evidence

ORD record
ord-f8da0fc1183b49efa24c906a43c73fe6
Source dataset
uspto-grants-2012_04
Patent number
US08153626B2

Reaction notes

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