3-Amino-1-propanol → HCID 11371014, compound

HRID 917746Notes

Reaction equation

HRID 917746 reaction equation
[F:1][C:2]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[C:6]([C:13]([OH:15])=O)=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=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>[F:1][C:2]1[CH:19]=[C:18]([CH3:20])[CH:17]=[CH:16][C:3]=1[NH:4][C:5]1[C:6]([C:13]([NH:33][CH2:34][CH2:35][CH2:36][OH:37])=[O:15])=[CH:7][N:8]([CH3:12])[C:9](=[O:11])[CH:10]=1

Participants

6

Reactant 3

HCID 90863-Amino-1-propanolHCID 682631,1'-CarbonyldiimidazoleHCID 23630798HCID 23630798, compound

Product 1

HCID 11371014HCID 11371014, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-(2-Fluoro-4-methylanilino)-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—10% MeOH/CH2Cl2 gradient elution) yielding 4-(2-fluoro-4-methylanilino)-N-(3-hydroxypropyl)-1-methyl-6-oxo-1,6-dihydro-3-pyridinecarboxamide (47%) as a pale cream solid; m.p. (EtOAc/Hexane) 142-145° C. 1H NMR [400 MHz, (CD3)2SO] δ 9.86 (br s, 1H), 8.36 (t, J=5.4 Hz, 1H), 8.21 (s, 1H), 7.30 (t, J=8.4 Hz, 1H), 7.16 (d, J=11.8 Hz, 1H), 7.05 (d, J=7.7 Hz, 1H), 5.40 (s, 1H), 4.48 (t, J=5.1 Hz, 1H), 3.47 (dd, J=11.5, 6.2 Hz, 2H), 3.35 (s, 3H), 3.27 (dd, J=12.8, 6.8 Hz, 2H), 2.32 (s, 3H), 1.67 (p, J=6.7 Hz, 2H). LCMS (ACPI−) 332 (100%). Anal. Calcd for C17H20FN3O3: C, 61.3; H, 6.1; N, 12.6. Found C, 61.0; H, 6.3; N, 12.7.

Workup

  1. customAfter workup, the residue was further purified by flash chromatography on silica gel (5% MeOH/CH2Cl2—10% MeOH/CH2Cl2 gradient elution)

Sources & evidence

ORD record
ord-f09e8c51c5b84593bc556ef1a83a22fa
Source dataset
uspto-grants-2007_09
Patent number
US07273877B2

Reaction notes

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