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

HRID 624912

Reaction equation

HRID 624912 reaction equation
C1([CH2:4][O:5][C:6]2[N:11]=[C:10]([C:12](O)=O)[CH:9]=CC=2OC(F)(F)F)CC1.[Cl:20][C:21]1[N:26]=[C:25]([C:27]([OH:29])=O)[CH:24]=[CH:23][C:22]=1[O:30][CH2:31][CH:32]1[CH2:34][CH2:33]1.CC1(C)COCN1>>[Cl:20][C:21]1[N:26]=[C:25]([C:27]([N:11]2[C:10]([CH3:12])([CH3:9])[CH2:4][O:5][CH2:6]2)=[O:29])[CH:24]=[CH:23][C:22]=1[O:30][CH2:31][CH:32]1[CH2:34][CH2:33]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 76284105(6-Chloro-5-cyclopropylmethoxy-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 (13 mg, 23%) as colorless oil; LC-MS (UV peak area, ESI) 100%, 311.1158 [MH+].

Workup

  1. customisolated (13 mg, 23%) as colorless oil

Sources & evidence

ORD record
ord-0de36d9c7245411c95f5cb90258b9047
Source dataset
uspto-grants-2016_04
Patent number
US09303012B2

Linked notes

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