Pyrazole → HCID 54149163, compound

HRID 1604298Notes

Reaction equation

[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][C:13]([CH:25]=[O:26])=[C:14]2Cl)[CH2:6]1)(=[O:3])[CH3:2].[NH:27]1[CH:31]=[CH:30][CH:29]=[N:28]1.C([O-])([O-])=O.[K+].[K+].C(O[C@H]1CC[C@@]2(C)C(=CC[C@@H]3[C@@H]2CC[C@@]2(C)[C@H]3CCC2N2C=CC=N2)C1)(=O)C>>[C:1]([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C:7](=[CH:8][CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][C:13]([CH:25]=[O:26])=[C:14]2[N:27]2[CH:31]=[CH:30][CH:29]=[N:28]2)[CH2:6]1)(=[O:3])[CH3:2]

Participants

Reactant 4

HCID 1048Pyrazole

HCID 11430Potassium Carbonate

HCID 1047470117-Chloro-16-formylandrosta-5,16-dien-3beta-yl acetate2×

HCID 54223629HCID 54223629, compound

Product 1

HCID 54149163HCID 54149163, compoundYield 62.8%

Procedure

Reaction of 3β-acetoxy-17-chloro-16-formylandrosta-5,16-diene (Compound 3) (0.5 g, 1.329 mmol), pyrazole (136 mg, 1.994 mmol) and K2CO3 (551 mg, 3.99 mmol) as described for Synthesis Example 7 after FCC (silica gel, pet. ether/EtOAc, (4:1)) gave a mixture (341 mg, approx. 3:1) of 3β-acetoxy-17-(1H-pyrazol-1-yl)-16-formylandrosta-5,16-diene and 3β-acetoxy-17-(1H-pyrazol-1-yl)androsta-5-ene. This mixture resisted separation by chromatography.

Sources & evidence

ORD record: ord-d339f9d643a242c0a9c329e0ce3751b0
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994335

Reaction notes

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