Hydroxylamine → HCID 67282013, compound

HRID 515499Notes

Reaction equation

HRID 515499 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C@H:9]2[CH2:15][N:14]([C:16]3[N:17]([CH3:29])[C:18](=[O:28])[CH:19]=[C:20]([C:22]4[CH:27]=[CH:26][N:25]=[CH:24][N:23]=4)[N:21]=3)[CH2:13][CH2:12][CH2:11][O:10]2)[CH:6]=[CH:7][CH:8]=1)#[N:2].NO.[C:32]1(C)C=CC=CC=1.C[O:40][CH:41](OC)[N:42](C)C>C(O)C>[CH3:29][N:17]1[C:18](=[O:28])[CH:19]=[C:20]([C:22]2[CH:27]=[CH:26][N:25]=[CH:24][N:23]=2)[N:21]=[C:16]1[N:14]1[CH2:13][CH2:12][CH2:11][O:10][C@@H:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]3[N:42]=[C:41]([CH3:32])[O:40][N:2]=3)[CH:4]=2)[CH2:15]1

Participants

6

Reactant 4

HCID 787HydroxylamineHCID 1140TolueneHCID 78373Dimethylformamide dimethyl acetalHCID 67281239HCID 67281239, compound

Product 1

HCID 67282013HCID 67282013, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (S)-2-[2-(3-cyano-phenyl)-[1,4]oxazepan-4-yl]-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (A039) (250 mg, 0.644 mmol) in ethanol (1.29 ml) was added 50 wt. %—hydroxylamine aqueous solution (128 mg, 1.93 mmol) at room temperature. The mixture was stirred at 80° C. for 2 hours and concentrated. The residue was partitioned between water and chloroform. The organic layer was dried over sodium sulfate and concentrated in vacuo. To the residue was added toluene (1.29 ml) and N,N-dimethylformamide dimethylacetal (190 mg, 1.29 mmol) at room temperature. After the mixture was refluxed for 2 hours, the solvent was evaporated. The residue was purified by silica gel column chromatography (eluant: chloroform/methanol=98/2) to afford (S)-1-Methyl-2-{2-[3-(5-methyl-[1,2,4]oxadiazol-3-yl)phenyl]-[1,4]oxazepan-4-yl}-1H-[4,4′]bipyrimidinyl-6-one (A030) as white solid (254 mg, 89%).

Workup

  1. concentrationconcentrated
  2. customThe residue was partitioned between water and chloroform
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. temperatureAfter the mixture was refluxed for 2 hours
  6. customthe solvent was evaporated
  7. customThe residue was purified by silica gel column chromatography (eluant: chloroform/methanol=98/2)

Sources & evidence

ORD record
ord-c1e0d7cea27f4d54ba22cc3c0947332e
Source dataset
uspto-grants-2015_08
Patent number
US09108957B2

Reaction notes

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