Cyclopropylamine → HCID 54698650, compound

HRID 2364170Notes

Reaction equation

HRID 2364170 reaction equation
[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:35])=[C:13]([C:30](OCC)=[O:31])[C:14](=[O:29])[N:15]2[CH2:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)=[N:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:36]1([NH2:39])[CH2:38][CH2:37]1>>[CH2:1]([C:8]1[CH:17]=[C:16]2[C:11]([C:12]([OH:35])=[C:13]([C:30]([NH:39][CH:36]3[CH2:38][CH2:37]3)=[O:31])[C:14](=[O:29])[N:15]2[CH2:18][C:19]2[CH:20]=[CH:21][C:22]([S:25]([CH3:28])(=[O:26])=[O:27])=[CH:23][CH:24]=2)=[N:10][CH:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 69828CyclopropylamineHCID 58882900HCID 58882900, compound

Product 1

HCID 54698650HCID 54698650, compound

Procedure

This compound was prepared from ethyl 7-benzyl-4-hydroxy-1-[4-(methylsulfonyl)benzyl]-2-oxo-1,2-dihydro-1,5-naphthyridine-3-carboxylate and cyclopropylamine employing methods similar to those described in Example 2. The product was obtained as a white solid: 1H NMR (CDCl3) δ 10.04 (1H, br d, J=3.4 Hz), 8.61 (1H, s), 7.81 (2H, d, J=8.4 Hz), 7.29 (3H, m), 7.17 (2H, d, J=8.4 Hz), 7.05 (1H, s), 7.03 (2H, m), 5.39 (2H, br), 4.05 (2H, s), 3.01 (3H, s), 2.97 (1H, m), 0.90 (2H, m), 0.70 (2H, m); HRMS calcd for C27H25N3O5S+H+: 504.1593. Found: 504.1581.

Workup

  1. customThe product was obtained as a white solid

Sources & evidence

ORD record
ord-9f990542dd3f4a14a3c0c7801266edfb
Source dataset
uspto-grants-2014_04
Patent number
US08691991B2

Reaction notes

Loading…