Methyl 6-morpholinonicotinate → HCID 178459828, compound

HRID 16736Notes

Reaction equation

HRID 16736 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C:8]1[N:13]=[CH:12][C:11]([C:14]([O:16]C)=O)=[CH:10][CH:9]=1)=[O:6])[CH:2]=[CH2:3].N1([C:24]2[N:29]=[CH:28][C:27]([C:30](OC)=O)=[CH:26][CH:25]=2)CCOCC1>>[CH3:5][O:4][C:1]1[CH:30]=[C:27]([CH2:26][CH2:25][C:24]2[CH:9]=[C:8]([NH:13][C:14]([C:11]3[CH:10]=[CH:9][C:8]([NH:7][C:5](=[O:6])[O:4][CH2:1][CH:2]=[CH2:3])=[N:13][CH:12]=3)=[O:16])[NH:7][N:29]=2)[CH:28]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 2776466Methyl 6-morpholinonicotinateHCID 57481282HCID 57481282, compound

Product 1

HCID 178459828HCID 178459828, compoundYield 37%

Procedure

Methyl 6-(prop-2-enoxycarbonylamino)pyridine-3-carboxylate, used as starting material was prepared in an analogous manner to the synthesis of methyl 6-morpholin-4-ylpyridine-3-carboxylate in Example 32, but starting with 6-(prop-2-enoxycarbonylamino)pyridine-3-carboxylic acid carboxylate (880 mg, 3.96 mmol) to give the title compound (0.35 g, 37%); 1H NMR (400.132 MHz, CDCl3) 3.93 (s, 3H), 4.75 (dt, 2H), 5.32 (dq, 1H), 5.41 (dq, 1H), 6.09-5.99 (m, 1H), 8.07 (d, 1H), 8.30 (dd, 1H), 8.97 (d, 1H), 9.45 (brs, 1H); MH+237.

Sources & evidence

ORD record
ord-01a08605bff54ee59d7359b89808baa9
Source dataset
uspto-grants-2010_06
Patent number
US07737149B2

Reaction notes

Loading…