Trifluoroacetic acid → HCID 73054872, compound

HRID 1778972Notes

Reaction equation

HRID 1778972 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:45])[CH2:10][C:11]1[CH:44]=[CH:43][CH:42]=[CH:41][C:12]=1[CH2:13][CH2:14][C:15]1[C:20]([C:21]([F:24])([F:23])[F:22])=[CH:19][N:18]=[C:17]([NH:25][C:26]2[CH:40]=[CH:39][C:29]([CH2:30][NH:31]C(=O)OC(C)(C)C)=[CH:28][CH:27]=2)[N:16]=1>C(Cl)Cl>[NH2:31][CH2:30][C:29]1[CH:28]=[CH:27][C:26]([NH:25][C:17]2[N:16]=[C:15]([CH2:14][CH2:13][C:12]3[CH:41]=[CH:42][CH:43]=[CH:44][C:11]=3[CH2:10][C:9]([NH2:8])=[O:45])[C:20]([C:21]([F:23])([F:24])[F:22])=[CH:19][N:18]=2)=[CH:40][CH:39]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712641HCID 86712641, compound

Product 1

HCID 73054872HCID 73054872, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

TFA (954 μL, 12.5 mmol) was added to a solution of tert-butyl 4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)benzylcarbamate (A16) (220 mg, 0.415 mmol) in DCM (10 mL) and the resulting mixture stirred for 20 hours at room temperature. The volatiles were removed in vacuo and the resulting residue partitioned between EtOAc (100 mL) and 2 M aqueous NaOH (100 mL). The layers were separated and the organic layer washed with water (100 mL), brine (50 mL), dried (MgSO4) then evaporated in vacuo to yield a white solid. The solid was taken up in DCM (10 mL) and sonicated for 2 minutes then petroleum benzine 40-60° C. (100 mL) was added and sonication continued for a further 10 minutes. The resulting suspension was filtered and the filter cake dried to give the title compound 3 as a white solid (135 mg, 76%); 1H NMR (400 MHz, d4-MeOH) δ 8.57 (s, 1H), 7.68 (d, J=8.6 Hz, 2H), 7.33 (d, J=8.8 Hz, 2H), 7.31-7.17 (m, 4H), 3.81 (s, 2H), 3.69 (s, 2H), 3.22-3.06 (m, 4H). LCMS-A: rt 4.722 min; m/z 428 [M−1]−.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe resulting residue partitioned between EtOAc (100 mL) and 2 M aqueous NaOH (100 mL)
  3. customThe layers were separated
  4. washthe organic layer washed with water (100 mL), brine (50 mL)
  5. dry with materialdried (MgSO4)
  6. customthen evaporated in vacuo
  7. customto yield a white solid
  8. customsonicated for 2 minutes
  9. customsonication
  10. waitcontinued for a further 10 minutes
  11. filtrationThe resulting suspension was filtered
  12. customthe filter cake dried

Sources & evidence

ORD record
ord-cb41119dc673409ca8ec2847a192dadb
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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