Trifluoroacetic acid → HCID 73055445, compound

HRID 1779002Notes

Reaction equation

HRID 1779002 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:50])[CH2:10][C:11]1[CH:49]=[CH:48][CH:47]=[CH:46][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:31]=[CH:30][C:29]([CH:32]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)=[C:28]([CH3:45])[CH:27]=2)[N:16]=1>C(Cl)Cl.C1CCCCC1>[CH3:45][C:28]1[CH:27]=[C:26]([NH:25][C:17]2[N:16]=[C:15]([CH2:14][CH2:13][C:12]3[CH:46]=[CH:47][CH:48]=[CH:49][C:11]=3[CH2:10][C:9]([NH2:8])=[O:50])[C:20]([C:21]([F:24])([F:22])[F:23])=[CH:19][N:18]=2)[CH:31]=[CH:30][C:29]=1[CH:32]1[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712660HCID 86712660, compound

Product 1

HCID 73055445HCID 73055445, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

TFA (1 mL) was added to a stirred solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-(trifluoromethyl)pyrimidin-2-yl)amino)-2-methylphenyl)piperidine-1-carboxylate (A43) (0.16 g, 0.27 mmol) in DCM (4 mL) and the resulting solution was stirred at room temperature for 16 hours. The volatiles were removed in vacuo and the residue was partitioned between EtOAc (10 mL) and 2 M aqueous NaOH (10 mL). The aqueous layer was extracted with EtOAc (2×10 mL) then and the combined organic layers were washed with water (10 mL), brine (10 mL) and dried over MgSO4. The volatiles were removed in vacuo to give a pale yellow solid. The solid was suspended in cyclohexane and the resulting suspension filtered to give the title compound 11 as a white solid (0.085 g, 64%); 1H NMR (400 MHz, d4-MeOH) δ 8.52 (s, 1H), 7.54 (dd, J=8.4, 2.2 Hz, 1H), 7.44 (d, J=2.1 Hz, 1H), 7.29-7.23 (m, 1H), 7.23-7.15 (m, 4H), 3.67 (s, 2H), 3.23-3.11 (m, 4H), 3.10-3.01 (m, 2H), 2.91 (tt, J=11.7, 3.8 Hz, 1H), 2.80 (td, J=12.3, 2.8 Hz, 2H), 2.35 (s, 3H), 1.84-1.59 (m, 4H). LCMS-A: rt 4.962 min; m/z 498.3 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was partitioned between EtOAc (10 mL) and 2 M aqueous NaOH (10 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×10 mL)
  4. washthe combined organic layers were washed with water (10 mL), brine (10 mL)
  5. dry with materialdried over MgSO4
  6. customThe volatiles were removed in vacuo
  7. customto give a pale yellow solid
  8. filtrationthe resulting suspension filtered

Sources & evidence

ORD record
ord-418ccdf225354ee79808e4ffe72bb933
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

Loading…