O-(cyclopropylmethyl)hydroxylamine hydrochloride → HCID 136359927, compound

HRID 1969657Notes

Reaction equation

HRID 1969657 reaction equation
[CH2:1]([C@H:3]1[C@@H:7]([C:8]2[N:12]3[C:13]4[CH:19]=[CH:18][NH:17][C:14]=4[N:15]=[CH:16][C:11]3=[N:10][N:9]=2)[CH2:6][C:5](=O)[CH2:4]1)[CH3:2].Cl.[CH:22]1([CH2:25][O:26][NH2:27])[CH2:24][CH2:23]1>CCO>[CH:22]1([CH2:25][O:26][N:27]=[C:5]2[CH2:6][C@H:7]([C:8]3[N:12]4[C:13]5[CH:19]=[CH:18][NH:17][C:14]=5[N:15]=[CH:16][C:11]4=[N:10][N:9]=3)[C@H:3]([CH2:1][CH3:2])[CH2:4]2)[CH2:24][CH2:23]1

Participants

4

Reactant 2

HCID 11557279O-(cyclopropylmethyl)hydroxylamine hydrochloride2×HCID 136009249HCID 136009249, compound

Product 1

HCID 136359927HCID 136359927, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone (0.05 g, 0.19 mmol, Example #AA.1.59) in EtOH (1 mL) was added TEA (0.04 mL, 0.28 mmol) and O-(cyclopropylmethyl)hydroxylamine hydrochloride (0.02 g, 0.19 mmol, Huhu Technologies). The reaction mixture was stirred for about 18 h at ambient temperature. Additional O-(cyclopropylmethyl)hydroxylamine hydrochloride (0.02 g, 0.19 mmol, Huhu Technologies) was added. The reaction was stirred at ambient temperature for about 5 h. The solvent was removed under reduced pressure. The crude material was purified by silica gel chromatography eluting with a gradient of 1-10% MeOH in DCM to afford (3R,4S)-3-ethyl-4-(6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyrazin-1-yl)cyclopentanone O-cyclopropylmethyl oxime (0.051 g, 80%): LC/MS (Table 1, Method a) Rt=1.94 min; MS m/z: 339 (M+H)+.

Workup

  1. stirringThe reaction was stirred at ambient temperature for about 5 h
  2. customThe solvent was removed under reduced pressure
  3. customThe crude material was purified by silica gel chromatography
  4. washeluting with a gradient of 1-10% MeOH in DCM

Sources & evidence

ORD record
ord-e4d744a9eb0c450abfbf56ad211c882f
Source dataset
uspto-grants-2013_04
Patent number
US08426411B2

Reaction notes

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