Trifluoroacetic acid → HCID 73056042, compound

HRID 1779104Notes

Reaction equation

HRID 1779104 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:43])[CH2:10][C:11]1[CH:42]=[CH:41][CH:40]=[CH:39][C:12]=1[CH2:13][CH2:14][C:15]1[C:20]([CH3:21])=[CH:19][N:18]=[C:17]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([CH:29]([NH:31]C(=O)OC(C)(C)C)[CH3:30])=[CH:25][CH:24]=2)[N:16]=1>C(Cl)Cl>[NH2:31][CH:29]([C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:17]2[N:16]=[C:15]([CH2:14][CH2:13][C:12]3[CH:39]=[CH:40][CH:41]=[CH:42][C:11]=3[CH2:10][C:9]([NH2:8])=[O:43])[C:20]([CH3:21])=[CH:19][N:18]=2)=[CH:24][CH:25]=1)[CH3:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712733HCID 86712733, compound

Product 1

HCID 73056042HCID 73056042, compoundYield 98.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of tert-butyl (1-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)phenyl)ethyl)carbamate (A132) (0.099 g, 0.20 mmol) in DCM (5 mL) and the resulting mixture stirred at room temperature for 3 hours. The volatiles were evaporated under reduced pressure then 2 M aqueous K2CO3 solution (10 mL) and water (15 mL) were added to the residue. The resulting suspension was sonicated for 1 minute, filtered and the filter cake dried to give the title compound 34 as a light tan solid (77 mg, 97%); 1H NMR (300 MHz, d6-DMSO) δ 9.26 (s, 1H), 8.15 (s, 1H), 7.67 (d, J=8.6 Hz, 2H), 7.42 (s, 1H), 7.23 (d, J=8.6 Hz, 2H), 7.14-7.23 (m, 4H), 6.92 (s, 1H), 3.92 (d, J=6.4 Hz, 1H), 3.50 (s, 2H), 3.32 (brs, 2H), 3.02-3.07 (m, 2H), 2.88-2.90 (m, 2H), 2.06 (s, 3H), 1.23 (d, J=6.5 Hz, 3H). LCMS-B: rt 4.691 min; m/z 390 [M+H]+.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. addition2 M aqueous K2CO3 solution (10 mL) and water (15 mL) were added to the residue
  3. customThe resulting suspension was sonicated for 1 minute
  4. filtrationfiltered
  5. customthe filter cake dried

Sources & evidence

ORD record
ord-41f85eb9788f4e9ba36a7aba758038fd
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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