6-Cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carboxylic acid → 6-Cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carboxylic acid [cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-amide

HRID 632284Notes

Reaction equation

HRID 632284 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[C:15]([F:18])([F:17])[F:16])[CH2:3][CH2:2]1.C1(N(C2N=C(C)ON=2)C)CC1.[CH:30]1([CH2:33][C@H:34]([NH2:41])[C:35]2[N:39]=[C:38]([CH3:40])[O:37][N:36]=2)[CH2:32]C1>>[CH:33]1([CH:34]([NH:41][C:12]([C:10]2[CH:9]=[CH:8][C:7]([C:15]([F:18])([F:17])[F:16])=[C:6]([O:5][CH2:4][CH:1]3[CH2:2][CH2:3]3)[N:11]=2)=[O:14])[C:35]2[N:39]=[C:38]([CH3:40])[O:37][N:36]=2)[CH2:30][CH2:32]1

Participants

4

Reactant 3

HCID 710874576-Cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carboxylic acidHCID 86674748(S)-2-Cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamineHCID 86674778Cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methylamine

Product 1

HCID 711056606-Cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carboxylic acid [cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-amide

Procedure

The title compound was synthesized in analogy to Example 1, using 6-cyclopropylmethoxy-5-trifluoromethyl-pyridine-2-carboxylic acid (Example 113 d) and cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methylamine (which can e.g. be prepared in a similar manner than (S)-2-cyclopropyl-1-(5-methyl-[1,2,4]oxadiazol-3-yl)-ethylamine (Example 38 e)) as starting materials, MS (EI): m/e=397.0 [M+H]+.

Sources & evidence

ORD record
ord-88ed89d6c98545d6aee4d6a674341162
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

Loading…