Ethyl azetidine-3-carboxylate → HCID 57523797, compound

HRID 2278804Notes

Reaction equation

HRID 2278804 reaction equation
[CH:1]1([C:6]2[CH:7]=[C:8]([CH:12]=[C:13]([O:15][CH3:16])[N:14]=2)[C:9]([OH:11])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:17][C:18]1[CH:19]=[C:20]([CH:25]=[C:26]([O:35][CH3:36])[C:27]=1[O:28][CH2:29][CH:30](OC)OC)[C:21](=[NH:24])[NH:22]O.[NH:37]1[CH2:40][CH:39]([C:41]([O:43]CC)=[O:42])[CH2:38]1>>[Cl:17][C:18]1[CH:19]=[C:20]([C:21]2[N:22]=[C:9]([C:8]3[CH:12]=[C:13]([O:15][CH3:16])[N:14]=[C:6]([CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[CH:7]=3)[O:11][N:24]=2)[CH:25]=[C:26]([O:35][CH3:36])[C:27]=1[O:28][CH2:29][CH2:30][N:37]1[CH2:40][CH:39]([C:41]([OH:43])=[O:42])[CH2:38]1

Participants

4

Reactant 3

HCID 21717027Ethyl azetidine-3-carboxylateHCID 58418037HCID 58418037, compoundHCID 178492428HCID 178492428, compound

Product 1

HCID 57523797HCID 57523797, compound

Procedure

The title compound is prepared starting from 2-cyclopentyl-6-methoxy-isonicotinic acid, 3-chloro-4-(2,2-dimethoxyethoxy)-N-hydroxy-5-methoxybenzimidamide and ethyl azetid ine-3-carboxylate in analogy to Example 43 and 1 (saponification); LC-MS: tR=0.88 min, [M+H]+=528.92; 1H NMR (CDCl3): δ 7.79 (d, J=1.5 Hz, 1H), 7.57 (d, J=1.4 Hz, 1H), 7.45 (s, 1H), 7.24 (s, 1H), 5.96 (s br, 1H), 4.55-4.64 (m, 2H), 4.44-4.54 (m, 2H), 4.32-4.38 (m, 2H), 4.00 (s, 6H), 3.65-3.74 (m, 1H), 3.58-3.65 (m, 2H), 3.18-3.27 (m, 1H), 2.05-2.14 (m, 2H), 1.82-1.94 (m, 4H), 1.75 (m, 2H).

Sources & evidence

ORD record
ord-d18d771baff34523af4206453964acdb
Source dataset
uspto-grants-2015_09
Patent number
US09133179B2

Reaction notes

Loading…