Nicotinic Acid → HCID 67298161, compound

HRID 1520306Notes

Reaction equation

HRID 1520306 reaction equation
[C:1]([OH:9])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=N[CH:3]=1.[NH2:10][C:11]1[C:19]([CH3:20])=[CH:18][C:17]([O:21][CH3:22])=[CH:16][C:12]=1[C:13]([NH2:15])=[O:14].[CH3:23]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>O.CN(C=O)C>[C:1]([NH:10][C:11]1[C:19]([CH3:20])=[CH:18][C:17]([O:21][CH3:22])=[CH:16][C:12]=1[C:13]([NH2:15])=[O:14])(=[O:9])[C:2]1[CH:3]=[CH:23][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 938Nicotinic AcidHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67298040HCID 67298040, compound

Product 1

HCID 67298161HCID 67298161, compoundYield 58.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A 50 mL round-bottom flask was charged with nicotinic acid (41 mg, 0.33 mmol, 1.0 eq.), 2-amino-5-methoxy-3-methylbenzamide (60 mg, 0.33 mmol, 1.0 eq.) and HBTU (190 mg, 0.50 mmol, 1.5 eq), which were suspended in 4 mL, of DMF. DIPEA (86 mg, 0.66 mmol, 2.0 eq.) was added dropwise at room temperature and the reaction mixture was stirred overnight. The reaction mixture was added to water (10 mL) dropwise with stirring. The mixture was extracted with ethyl acetate. The ethyl acetate was evaporated and 55 mg of the orange solid (58.5% yield) was obtained. LCMS m/z=286.1 (M+1) (Method B) (retention time=1.24 min).

Workup

  1. stirringwith stirring
  2. extractionThe mixture was extracted with ethyl acetate
  3. customThe ethyl acetate was evaporated

Sources & evidence

ORD record
ord-63d4770a09cc4b42a1c5989b10b4815b
Source dataset
uspto-grants-2015_07
Patent number
US09073890B2

Reaction notes

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