Cyclopropylamine → HCID 117738985, compound

HRID 1507144Notes

Reaction equation

[CH2:1]([N:8]([CH3:29])[CH2:9][CH2:10][CH2:11][N:12]([CH2:20][C:21]1[CH:26]=[C:25]([CH:27]=O)[CH:24]=[CH:23][N:22]=1)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]1([NH2:33])[CH2:32][CH2:31]1>>[CH2:1]([N:8]([CH3:29])[CH2:9][CH2:10][CH2:11][N:12]([CH2:20][C:21]1[CH:26]=[C:25]([CH2:27][NH:33][CH:30]2[CH2:32][CH2:31]2)[CH:24]=[CH:23][N:22]=1)[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 90374985HCID 90374985, compound

Product 1

HCID 117738985HCID 117738985, compound

Procedure

By General Procedure A from tert-butyl N-{3-[benzyl(methyl)amino]propyl}-N-[(4-formylpyridin-2-yl)methyl]carbamate and cyclopropanamine. Purification by column chromatography using DCM:MeOH:NH4OH (8:2:1) gave the title compound. 1H NMR (300 MHz, CDCl3), (rotamers) δ ppm: 8.4 (d, 1H), 7.4-7.2 (m, 7H), 4.5 (s, 2H), 3.9 (s, 2H), 3.7-3.2 (m, 4H), 2.6-1.7 (m, 8H), 1.4 (d, 9H), 0.6-01.3 (m, 4H).

Workup

customPurification by column chromatography

Sources & evidence

ORD record: ord-9f5c589c054a42309c6f8a365d8cddab
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221801B2

Reaction notes

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