Pyridine → HCID 90111905, compound

HRID 521731Notes

Reaction equation

HRID 521731 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:16][CH:15]3[C:10]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)([N:11]=[C:12]([NH:17]C(=O)C4C=CC=CC=4)[S:13][CH2:14]3)[CH2:9]2)=[N:6][CH:7]=1.N1C=CC=CC=1.Cl.CON>C(O)C>[F:1][C:2]1[CH:7]=[N:6][C:5]([N:8]2[CH2:16][CH:15]3[C:10]([C:26]4[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=4)([N:11]=[C:12]([NH2:17])[S:13][CH2:14]3)[CH2:9]2)=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 521874O-Methylhydroxylamine hydrochlorideHCID 90111877HCID 90111877, compound

Product 1

HCID 90111905HCID 90111905, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of N-[6-(5-fluoropyrimidin-2-yl)-7a-(3-pyridyl)-4,4a,5,7-tetrahydropyrrolo[3,4-d][1,3]thiazin-2-yl]benzamide (110 mg, 0.210 mmol) in ethanol (10 mL) are added pyridine (187 μL 2.31 mmol) and O-methylhydroxylamine hydrochloride (143 mg, 1.68 mmol). The mixture is heated at 70° C. with stirring for 17 hours. The solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using a 0-10% gradient of 0.14 M ammonia/methanol solution in dichloromethane to give the title compound (62 mg, 89%). ES/MS (m/e): 331 (M+1).

Workup

  1. customThe solvent is removed under reduced pressure
  2. customThe residue is purified by silica gel chromatography

Sources & evidence

ORD record
ord-4ccd2433e89f4e778e9e73294f4c7295
Source dataset
uspto-grants-2016_05
Patent number
US09328124B2

Reaction notes

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