Trifluoroacetic acid → HCID 73054868, compound

HRID 1779038Notes

Reaction equation

HRID 1779038 reaction equation
[NH2:1][C:2](=[O:41])[CH2:3][C:4]1[CH:40]=[CH:39][CH:38]=[CH:37][C:5]=1[CH2:6][CH2:7][C:8]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:11]=[C:10]([NH:18][C:19]2[CH:36]=[CH:35][C:22]([CH2:23][N:24]([CH2:32][CH2:33][OH:34])C(=O)OC(C)(C)C)=[CH:21][CH:20]=2)[N:9]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[OH:34][CH2:33][CH2:32][NH:24][CH2:23][C:22]1[CH:21]=[CH:20][C:19]([NH:18][C:10]2[N:9]=[C:8]([CH2:7][CH2:6][C:5]3[CH:37]=[CH:38][CH:39]=[CH:40][C:4]=3[CH2:3][C:2]([NH2:1])=[O:41])[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][N:11]=2)=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712685HCID 86712685, compound

Product 1

HCID 73054868HCID 73054868, compoundYield 23.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl 4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzyl(2-hydroxyethyl)carbamate (A75) (0.301 g, 0.525 mmol) and trifluoroacetic acid (1.0 mL) in DCM (10 mL) was stirred at room temperature for 22 hours. The volatiles were removed in vacuo and 2 M aqueous sodium hydroxide solution (20 mL) added to the residue. The resulting suspension was sonicated for several minutes then filtered, washing the filter cake with water. Semi preparative HPLC of the filter cake gave the title compound 19 as a white solid (58 mg, 23%); 1H NMR (300 MHz, d4-MeOH) δ 8.61 (s, 1H), 8.53 (s, 1H), 7.83 (d, J=8.5 Hz, 2H), 7.46 (d, J=8.6 Hz, 2H), 7.29-7.19 (m, 4H), 4.19 (s, 2H), 3.82 (t, J=5.2 Hz, 2H), 3.68 (s, 2H), 3.22-3.10 (m, 6H). LCMS-B: rt 5.313 min; m/z 474 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo and 2 M aqueous sodium hydroxide solution (20 mL)
  2. additionadded to the residue
  3. customThe resulting suspension was sonicated for several minutes
  4. filtrationthen filtered
  5. washwashing the filter cake with water

Sources & evidence

ORD record
ord-a9bd926a62d8401eaccc9e8c278c11e7
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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