Trifluoroacetic acid → HCID 18548745, compound

HRID 1266897Notes

Reaction equation

C(OC(=O)[NH:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH:18]=[CH:17][CH:16]=[CH:15]2)=[CH:10][C:9]=1[NH2:19])(C)(C)C.C(O[C:26](=[O:38])[CH2:27][C:28]([C:30]1[CH:35]=[CH:34][N:33]=[C:32]([C:36]#[N:37])[CH:31]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C1(C)C=CC=CC=1.C(Cl)Cl>[O:38]=[C:26]1[CH2:27][C:28]([C:30]2[CH:35]=[CH:34][N:33]=[C:32]([C:36]#[N:37])[CH:31]=2)=[N:7][C:8]2[CH:13]=[CH:12][C:11]([N:14]3[CH:18]=[CH:17][CH:16]=[CH:15]3)=[CH:10][C:9]=2[NH:19]1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (2-amino-4-pyrrol-1-yl-phenyl)-carbamic acid tert-butyl ester (Example J2) (0.14 g) and 3-(2-cyano-pyridin-4-yl)-3-oxo-propionic acid tert-butyl ester (Example K3) (0.14 g) in toluene (1.5 mL) was heated to 100° C. for 4 h, a fine precipitate being formed. The mixture was cooled and the precipitae was isolated by filtration. A solution of this solid in CH2Cl2 (2.5 mL) and TFA (2.5 mL) was stirred for 0.5 h at 20° C. and then evaporated in vacuum. The residual oil was dissolved in AcOEt and the solution was washed with saturated Na2CO3 solution and with brine, dried over Na2SO4 and evaporated in vacuum. The solid residue was triturated with CH2Cl2 to give the title compound (0.06 g) as light-yellow crystals.

Workup

customa fine precipitate being formed
temperatureThe mixture was cooled
customthe precipitae was isolated by filtration
customevaporated in vacuum
dissolutionThe residual oil was dissolved in AcOEt
washthe solution was washed with saturated Na2CO3 solution and with brine
dry with materialdried over Na2SO4
customevaporated in vacuum
customThe solid residue was triturated with CH2Cl2

Sources & evidence

ORD record: ord-c12761b58c5747db91a8c8048380bf43
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06548495B2

Reaction notes

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