3-Amino-1-propanol → HCID 11749883, compound

HRID 917752Notes

Reaction equation

HRID 917752 reaction equation
[Br:1][C:2]1[CH:19]=[CH:18][C:5]([NH:6][C:7]2[C:8]([C:15]([OH:17])=O)=[CH:9][N:10]([CH3:14])[C:11](=[O:13])[CH:12]=2)=[C:4]([F:20])[CH:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[NH2:33][CH2:34][CH2:35][CH2:36][OH:37]>C1COCC1.CN(C=O)C>[Br:1][C:2]1[CH:19]=[CH:18][C:5]([NH:6][C:7]2[C:8]([C:15]([NH:33][CH2:34][CH2:35][CH2:36][OH:37])=[O:17])=[CH:9][N:10]([CH3:14])[C:11](=[O:13])[CH:12]=2)=[C:4]([F:20])[CH:3]=1

Participants

6

Reactant 3

HCID 90863-Amino-1-propanolHCID 682631,1'-CarbonyldiimidazoleHCID 115809254-(4-Bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylic acid

Product 1

HCID 11749883HCID 11749883, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(4-Bromo-2-fluoroanilino)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxylic acid and CDI were dissolved in a mixture of anhydrous THF and anhydrous DMF and treated with 3-amino-1-propanol as for example 34. After workup, the residue was further purified by flash chromatography on silica gel (5% MeOH/CH2Cl2) to give 4-(4-bromo-2-fluoroanilino)-N-(3-hydroxypropyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (71%) as a cream solid; m.p. (EtOAc/Hexane) 167-170° C. 1H NMR [400 MHz, (CD3)2SO] δ 10.10 (br s, 1H), 8.40 (t, J=5.3 Hz, 1H), 8.24 (s, 1H), 7.69-7.64 (m, 1H), 7.48-7.40 (m, 2H), 5.56 (s, 1H), 4.48 (t, J=5.1 Hz, 1H), 3.47 (dd, J=11.5, 6.2 Hz, 2H), 3.37 (s, 3H), 3.27 (dd, J=12.7, 6.9 Hz, 2H), 1.67 (p, J=6.7 Hz, 2H). LCMS (ACPI−) 398 (85%), 396 (100%). Anal. Calcd for C16H17BrFN3O3: C, 48.3; H, 4.3; N, 10.6. Found C, 48.2; H, 4.2; N, 10.5.

Workup

  1. customAfter workup, the residue was further purified by flash chromatography on silica gel (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d1f85594a22b4ba6873460288317fe3f
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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