Cyclopropylamine → HCID 90375026, compound

HRID 1507148Notes

Reaction equation

[CH:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]([CH2:18][C:19](=[O:36])[NH:20][CH:21]2[CH2:26][CH2:25][N:24]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[O:34][CH3:35])[CH2:23][CH2:22]2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH:4]=1)=O.[CH:37]1([NH2:40])[CH2:39][CH2:38]1>>[CH:37]1([NH:40][CH2:1][C:3]2[CH:8]=[CH:7][N:6]=[C:5]([CH2:9][N:10]([CH2:18][C:19](=[O:36])[NH:20][CH:21]3[CH2:22][CH2:23][N:24]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH3:35])[CH2:25][CH2:26]3)[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[CH:4]=2)[CH2:39][CH2:38]1

Participants

Reactant 2

HCID 69828Cyclopropylamine

HCID 90375145HCID 90375145, compound

Product 1

HCID 90375026HCID 90375026, compound

Procedure

By General Procedure A from tert-butyl N-[(4-formylpyridin-2-yl)methyl]-N-[({1-[(2-methoxyphenyl)methyl]piperidin-4-yl}carbamoyl)methyl]carbamate and cyclopropylamine. Purification by column chromatography (CH2Cl2/MeOH/NH4OH, 90:10:1) gave the title compound as a colorless glue. 1H NMR (300 MHz, CDCl3): δ 9.40 (br s, 1H), 8.62 (2S, 1H; rotamer), 8.40 (s, 1H), 7.50-7.40 (m, 2H), 7.38 (m, 1H), 7.20 (m, 1H), 7.00-6.80 (m, 2H), 4.58 & 4.48 (2S, 2H; rotamer), 4.00-3.60 (m, 8H), 3.18-2.99 (m, 4H), 2.40-2.20 (m, 2H), 1.80 (m, 2H), 1.70 (m, 2H), 1.40 & 1.20 (2S, 9H; rotamer), 1.00 (m, 4H).

Workup

customPurification by column chromatography (CH2Cl2/MeOH/NH4OH, 90:10:1)

Sources & evidence

ORD record: ord-520cf4377dcf4d00842003413ed85d0f
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09221801B2

Reaction notes

Loading…