4,4-Dimethyl oxazolidine → (6-Cyclopropylmethoxy-5-trifluoromethoxy-pyridin-2-yl)-(4,4-dimethyl-oxazolidin-3-yl)-methanone

HRID 624911Notes

Reaction equation

HRID 624911 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([OH:14])=O)[CH:9]=[CH:8][C:7]=2[O:15][C:16]([F:19])([F:18])[F:17])[CH2:3][CH2:2]1.ClC1N=C(C(O)=O)C=CC=1OCC1CC1.[CH3:35][C:36]1([CH3:41])[CH2:40][O:39][CH2:38][NH:37]1>>[CH:1]1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12]([N:37]3[C:36]([CH3:41])([CH3:35])[CH2:40][O:39][CH2:38]3)=[O:14])[CH:9]=[CH:8][C:7]=2[O:15][C:16]([F:19])([F:18])[F:17])[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 620104,4-Dimethyl oxazolidineHCID 902025746-Cyclopropylmethoxy-5-trifluoromethoxy-pyridine-2-carboxylic acidHCID 902026096-Chloro-5-cyclopropylmethoxy-pyridine-2-carboxylic acid

Product 1

HCID 76282370(6-Cyclopropylmethoxy-5-trifluoromethoxy-pyridin-2-yl)-(4,4-dimethyl-oxazolidin-3-yl)-methanone

Procedure

The title compound was synthesized in analogy to Example 47 b, using the mixture of 6-cyclopropylmethoxy-5-trifluoromethoxy-pyridine-2-carboxylic acid and 6-chloro-5-cyclopropylmethoxy-pyridine-2-carboxylic acid (Example 47 a, 50 mg, 180 μmol) and 4,4-dimethyl-oxazolidine (CAN 51200-87-4; 28.4 μl (75%), 198 μmol) as starting materials and isolated (24 mg, 37%) as colorless oil; LC-MS (UV peak area, ESI) 100%, 361.1370 [MH+].

Workup

  1. customisolated (24 mg, 37%) as colorless oil

Sources & evidence

ORD record
ord-0860312ac4f74f5186e6d84652ce2168
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Reaction notes

Loading…