Acetic Acid → HCID 54575574, compound

HRID 1519247Notes

Reaction equation

HRID 1519247 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH:21]=O)=[N:6][CH:7]=1.[NH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)=[N:11][C:10]=2[CH2:21][NH:23][C:24]2[CH:25]=[CH:26][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:32][CH:33]=2)=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 12082Methyl 4-aminobenzoateHCID 5049666Sodium triacetoxyborohydrideHCID 86675604HCID 86675604, compound2×

Product 1

HCID 54575574HCID 54575574, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Procedure

To a solution of 5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazole-4-carbaldehyde (intermediate B4:1, 0.02 g, 0.06 mmol) in DCE was added methyl 4-aminobenzoate (0.01 g, 0.06 mmol), acetic acid (3.4 ul, 0.06 mmol) and NaBH(OAc)3 (0.015 g, 0.07 mmol). After Stirring at rt overnight, a drop of water was added to the reaction and purified by reverse phase HPLC to give methyl 4-[({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methyl)amino]benzoate. 1H NMR (400 MHz, CDCl3) δ 8.35 (d, J=2.5 Hz, 1H), 8.05 (m, 2H), 737 (d, J=8.8 Hz, 2H), 7.44 (dd, J=8.4, 2.5 Hz, 1H), 7.14 (m, 2H), 6.90 (d, J=8.4 Hz, 1H), 6.61 (d, 3=8.8 Hz, 2H), 4.43 (s, 2H), 3.84 (s, 3H); HRMS exact mass calc for C23H17ClFN3O3S [M+H]: 470.0736; observed: 470.0734.

Workup

  1. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-ed5ca35b15d84734b4665485502fe792
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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