Hydroxylamine → (NE)-N-[(6-chloro-3-methoxy-1-tritylpyrazolo[4,3-c]pyridin-4-yl)methylidene]hydroxylamine

HRID 588139Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([CH:8]=O)[C:5]2[C:10]([O:32][CH3:33])=[N:11][N:12]([C:13]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:4]=2[CH:3]=1.C([O-])(=O)C.[Na+].[NH2:39][OH:40]>C(O)C>[Cl:1][C:2]1[N:7]=[C:6](/[CH:8]=[N:39]/[OH:40])[C:5]2[C:10]([O:32][CH3:33])=[N:11][N:12]([C:13]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde (11B, 100 mg, 0.220 mmol), sodium acetate (54.2 mg, 0.661 mmol), and hydroxylamine (21.8 mg, 0.331 mmol) were taken up in Ethanol (2.2 ml). The reaction was allowed to stir at 70° C. for 1 hour. Room temperature was attained and the reaction mixture was concentrated in vacuo. The mixture was partitioned between EtOAc and saturated NaHCO3. The combined orgniac layers were washed with brine, dried over MgSO4, and concentrated in vacuo to give (E)-6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbaldehyde oxime. The products were carried forward without purification. MS: [M+H]+ m/z 469.

Workup

customRoom temperature
concentrationthe reaction mixture was concentrated in vacuo
customThe mixture was partitioned between EtOAc and saturated NaHCO3
washThe combined orgniac layers were washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-80d15d8525c24b97972fa7439926ba73
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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