Cyclopropylamine → HCID 70805129, compound

HRID 1519043Notes

Reaction equation

[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][N:4]([CH3:9])[C:3]=1[CH:10](O)[C:11]([F:14])([F:13])[F:12].[CH:16]1([NH2:19])[CH2:18][CH2:17]1>>[CH:16]1([NH:19][CH:10]([C:3]2[N:4]([CH3:9])[CH:5]=[CH:6][C:7](=[O:8])[C:2]=2[OH:1])[C:11]([F:14])([F:13])[F:12])[CH2:18][CH2:17]1

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 67282261HCID 67282261, compound

Product 1

HCID 70805129HCID 70805129, compoundYield 40%

Procedure

In a similar manner, Apo7074 was prepared from 3-hydroxy-1-methyl-2-(2,2,2-trifluoro-1-hydroxyethyl)pyridin-4(1H)-one (1.0 g, 4.5 mmol) and cyclopropylamine (0.62 mL, 9.0 mmol). The title compound Apo7074 (470 mg) was obtained after purification by flash chromatography (5% MeOH in CH2Cl2 as eluant). Yield=40%; 1H NMR (400 MHz, DMSO+a few drops of D2O) δ (ppm): 7.67 (d, J=6.8 Hz, 1H), 6.25 (d, J=7.1 Hz, 1H), 4.70 (q, J=8.1 Hz, 1H), 3.74 (s, 3H), 2.04 (br. s., 1H), 0.34-0.43 (m, 4H); MS m/z 263 [M+1]+, 206 (100%).

Sources & evidence

ORD record: ord-4aaaa1da2b9a4f1182d45d17eddd279d
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073865B2

Reaction notes

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