Trifluoroacetic acid → HCID 73056041, compound

HRID 1779100Notes

Reaction equation

HRID 1779100 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]([CH3:21])=[CH:19][N:18]=[C:17]([NH:22][C:23]2[CH:24]=[N:25][N:26]([CH:28]3[CH2:33][CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30][CH2:29]3)[CH:27]=2)[N:16]=1>C(Cl)Cl>[CH3:21][C:20]1[C:15]([CH2:14][CH2:13][C:12]2[CH:41]=[CH:42][CH:43]=[CH:44][C:11]=2[CH2:10][C:9]([NH2:8])=[O:45])=[N:16][C:17]([NH:22][C:23]2[CH:24]=[N:25][N:26]([CH:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)[CH:27]=2)=[N:18][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712732HCID 86712732, compound

Product 1

HCID 73056041HCID 73056041, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL) was added to a solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)-1H-pyrazol-1-yl)piperidine-1-carboxylate (A128) (0.040 g, 0.077 mmol) in DCM (5 mL) and the resulting mixture stirred for 18 hours at room temperature. The volatiles were evaporated under reduced pressure and the residue partitioned between 2 M NaOH (10 mL) and EtOAc (25 mL). The organic layer was separated and washed with water (25 mL), brine (25 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound 33 as an off white solid (0.015 g, 49%); 1H NMR (400 MHz, d4-MeOH) δ 8.05 (s, 1H), 7.99 (d, J=0.5 Hz, 1H), 7.56 (d, J=0.6 Hz, 1H), 7.27-7.22 (m, 1H), 7.22-7.15 (m, 3H), 4.23 (tt, J=11.7, 4.1 Hz, 1H), 3.64 (s, 2H), 3.23-3.09 (m, 4H), 3.02-2.91 (m, 2H), 2.76 (td, J=12.8, 2.5 Hz, 2H), 2.14-2.05 (m, 5H), 1.98-1.85 (m, 2H). LCMS-A: rt 3.968 min; m/z 420 [M+H]+.

Workup

  1. customThe volatiles were evaporated under reduced pressure
  2. customthe residue partitioned between 2 M NaOH (10 mL) and EtOAc (25 mL)
  3. customThe organic layer was separated
  4. washwashed with water (25 mL), brine (25 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-7a74177c2284481aa6deeb3ae89bc970
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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