Trifluoroacetic acid → HCID 66896930, compound

HRID 541949Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([N:11]([CH2:28][C:29]1[CH:30]=[C:31]([NH:35]C(=O)OC(C)(C)C)[CH:32]=[CH:33][CH:34]=1)[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([NH:19][C:20]2[C:25]([Cl:26])=[CH:24][N:23]=[C:22](Cl)[N:21]=2)[CH:14]=1)(=[O:10])[CH3:9].FC(F)(F)C(O)=O>C(#N)C>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([N:11]1[CH2:28][C:29]2[CH:30]=[C:31]([CH:32]=[CH:33][CH:34]=2)[NH:35][C:22]2=[N:21][C:20](=[C:25]([Cl:26])[CH:24]=[N:23]2)[NH:19][C:15]2=[CH:14][C:13](=[CH:18][CH:17]=[CH:16]2)[CH2:12]1)(=[O:10])[CH3:9]

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of tert-butyl {3-[(acetyl {3-[(2,5-dichloropyrimidin-4-yl)amino]benzyl}amino)methyl]phenyl}carbamate trifluoroacetate (10 mg, 16 μmol) in acetonitrile (1.5 mL) was treated with trifluoroacetic acid (75 μL, 0.97 mmol) and heated at 70° C. for 16 h. The reaction mixture was cooled and purified by preparative LCMS to give the desired product (2.5 mg, 32%) as a solid. LCMS for C20H19ClN5O (M+H)+: m/z=380.0. 1H NMR (300 MHz, CD3OD): δ 8.14 (d, J=1.8 Hz, 1H), 7.78 (s, 1H), 7.63-7.61 (m, 1H), 7.40-7.21 (m, 2H), 7.19-7.05 (m, 3H), 6.98-6.96 (m, 1H), 4.71-4.62 (m, 4H).

Workup

temperatureThe reaction mixture was cooled
custompurified by preparative LCMS

Sources & evidence

ORD record: ord-663052cab80e4f02bb20219b19b273fb
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871753B2

Reaction notes

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