Trichloroacetonitrile → HCID 59143732, compound

HRID 2400368Notes

Reaction equation

[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[NH2:8].[CH2:9]([O:16][C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=O)=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClC(Cl)(Cl)C#N>C(#N)C>[CH2:9]([O:16][C:17]1[CH:18]=[CH:19][C:20]([C:21]2[O:1][C:2]3[CH:7]=[CH:6][N:5]=[CH:4][C:3]=3[N:8]=2)=[CH:24][CH:25]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a cooled (0° C.) suspension of commercially available 4-hydroxy-3-amino-pyridine (14, 19.3 g, 175 mmol) in acetonitril (1500 ml) was added 4-benzyloxy-benzoic acid (24, Ra=Rb=H, 40 g, 175 mmol), triphenylphosphine (142.5 g, 543 mmol, 3.1 eq) and trichloroactonitril (54.5 ml, 543 mmol, 3.1 eq). The reaction mixture was allowed to reach room temperature and the mixture was stirred for 16 hrs at 80° C. The mixture was concentrated in vacuo and the residues was dissolved in DCM and washed with 2N NaOH (3×). The combined water layers were extracted with DCM and the organic layers dried (Na2SO4) to give crude 25 (Ra=Rb=H) as oil which was used in the next step without further purification.

Workup

temperatureTo a cooled
customto reach room temperature
concentrationThe mixture was concentrated in vacuo
dissolutionthe residues was dissolved in DCM
washwashed with 2N NaOH (3×)
extractionThe combined water layers were extracted with DCM
dry with materialthe organic layers dried (Na2SO4)
customto give crude 25 (Ra=Rb=H) as oil which
customwas used in the next step without further purification

Sources & evidence

ORD record: ord-3e4d6e291ad646c99c771f83574d55bd
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796262B2

Reaction notes

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