5-Cyclopropyl-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acid → 5-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid [cyclopropyl-(5-methyl-[1,2,4]oxadiazol-3-yl)-methyl]-amide

HRID 632272Notes

Reaction equation

HRID 632272 reaction equation
[CH:1]1([C:4]2[CH:5]=[CH:6][C:7]([C:18]([OH:20])=O)=[N:8][C:9]=2[O:10][CH2:11][CH:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[CH2:3][CH2:2]1.C1(C2C=CC(C(O)=O)=NC=2OCC2CCCO2)CC1.C1(N(C2N=C(C)ON=2)C)CC1.[CH:51]1([CH2:54][C@H:55]([NH2:62])[C:56]2[N:60]=[C:59]([CH3:61])[O:58][N:57]=2)[CH2:53]C1>>[CH:54]1([CH:55]([NH:62][C:18]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]3[CH2:2][CH2:3]3)=[C:9]([O:10][CH2:11][CH:12]3[CH2:13][CH2:14][O:15][CH2:16][CH2:17]3)[N:8]=2)=[O:20])[C:56]2[N:60]=[C:59]([CH3:61])[O:58][N:57]=2)[CH2:51][CH2:53]1

Participants

5

Reactant 4

HCID 710872545-Cyclopropyl-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acidHCID 710875605-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-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 711056515-Cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-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 5-cyclopropyl-6-(tetrahydro-pyran-4-ylmethoxy)-pyridine-2-carboxylic acid (which can e.g. be prepared in a similar manner than 5-cyclopropyl-6-(tetrahydro-furan-2-ylmethoxy)-pyridine-2-carboxylic acid (Example 166 b)) 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=413.1 [M+H]+.

Sources & evidence

ORD record
ord-b4d8fd87944141bebf326790deb9643e
Source dataset
uspto-grants-2016_04
Patent number
US09321727B2

Reaction notes

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