Trifluoroacetic acid → HCID 118162118, compound

HRID 1749478Notes

Reaction equation

HRID 1749478 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:31]=[CH:32][CH:33]=1)[CH2:5][CH2:6][NH:7][C:8]1[N:13]=[C:12]([NH:14][C@H:15]2[CH2:18][C@H:17]([NH:19]C(=O)OC(C)(C)C)[C:16]2([CH3:28])[CH3:27])[C:11]([C:29]#[N:30])=[CH:10][N:9]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:19][C@H:17]1[CH2:18][C@H:15]([NH:14][C:12]2[C:11]([C:29]#[N:30])=[CH:10][N:9]=[C:8]([NH:7][CH2:6][CH2:5][C:4]3[CH:31]=[CH:32][CH:33]=[C:2]([Cl:1])[CH:3]=3)[N:13]=2)[C:16]1([CH3:28])[CH3:27]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131733587HCID 131733587, compound

Product 1

HCID 118162118HCID 118162118, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl ((1S,3S)-3-((2-((3-chlorophenethyl)amino)-5-cyanopyrimidin-4-yl)amino)-2,2-dimethylcyclobutyl)carbamate (100 mg, 0.21 mmol) in dry DCM (2 mL) was added TFA (1.5 mL) dropwise under cooling in an ice-water bath. The resulting mixture was stirred at room temperature for 30 min. After removal of the organic solvents, the residue was neutralized with ammonia and extracted with DCM. The combined organic layers were dried over anhydrous sodium sulfate and concentrated to give the crude product, which was purified by standard methods to afford the title compound (49.7 mg, 0.13 mmol, 64% yield). 1H NMR (400 MHz, CD3OD) δ (ppm) 8.06 (s, 1H), 7.29-7.15 (m, 4H), 4.33 (dd, J1=5.6 Hz, J2=9.2 Hz, 1H), 3.72-3.50 (m, 2H), 3.18-3.12 (m, 1H), 2.93-2.86 (m, 2H), 2.45-2.39 (m, 1H), 2.17-2.12 (m, 1H), 1.20 (s, 3H), 0.98 (s 3H). MS (ESI) m/z 371.2 [M+H]+.

Workup

  1. temperatureunder cooling in an ice-water bath
  2. customAfter removal of the organic solvents
  3. extractionextracted with DCM
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give the crude product, which
  7. customwas purified by standard methods

Sources & evidence

ORD record
ord-5219b07ee8734b77b9aef6a8b8f1ca76
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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