Triethylamine → 2-Methoxy-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid

HRID 1039741Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([C:10]([OH:12])=[O:11])=[C:4]([CH3:13])[CH:3]=1.CN(C([O:21]N1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:38][CH2:39][N:40](CC)[CH2:41][CH3:42].FC1C=C(C=C(F)C=1)CN>C1COCC1.CCOC(C)=O>[CH3:9][O:8][C:6]1[C:5]([C:10]([OH:12])=[O:11])=[C:4]([CH3:13])[CH:3]=[C:2]([N:40]2[CH2:41][CH2:42][O:21][CH2:38][CH2:39]2)[N:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 302 mg crude 6-chloro-2-methoxy-4-methyl-pyridine-3-carboxylic acid in THF (12 ml) were added 568 mg (1.5 mmol) HATU and 934 μl (6.8 mmol) NEt3. The RM was stirred at 50° C. for 3 h followed by the addition of 268 mg (1.9 mmol) 3,5-difluorobenzylamine. Stirring was continued at 50° C. for 72 h. The RM was then diluted with EtOAc (50 ml) and subsequently washed with a 4M aq. NH4Cl sol., a 1M aq. NaHCO3 sol. and brine. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification of the residue by CC (hexane/EtOAc 3:1) provided 237 mg (0.7 mmol, 54% over 2 steps) 2-methoxy-4-methyl-6-morpholin-4-yl-pyridine-3-carboxylic acid.

Workup

stirringStirring
waitwas continued at 50° C. for 72 h
washsubsequently washed with a 4M aq. NH4Cl sol.
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated in vacuo
customPurification of the residue by CC (hexane/EtOAc 3:1)

Sources & evidence

ORD record: ord-e5af66282fdb41c8aed9a20e95e82396
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08552200B2

Reaction notes

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