Trifluoroacetic acid → HCID 73054873, compound

HRID 1778977Notes

Reaction equation

HRID 1778977 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:46])[CH2:10][C:11]1[CH:45]=[CH:44][CH:43]=[CH:42][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]=[CH:25][C:26]([CH:29]3[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]3)=[N:27][CH:28]=2)[N:16]=1>C(Cl)Cl>[CH3:21][C:20]1[C:15]([CH2:14][CH2:13][C:12]2[CH:42]=[CH:43][CH:44]=[CH:45][C:11]=2[CH2:10][C:9]([NH2:8])=[O:46])=[N:16][C:17]([NH:22][C:23]2[CH:28]=[N:27][C:26]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)=[CH:25][CH:24]=2)=[N:18][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712645HCID 86712645, compound

Product 1

HCID 73054873HCID 73054873, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.5 mL) was added to a solution of tert-butyl 4-(5-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)pyridin-2-yl)piperidine-1-carboxylate (A20) (70 mg, 0.13 mmol) in DCM (5 mL) and the resulting mixture stirred for 18 hours at room temperature. The volatiles were removed in vacuo and the residue partitioned between 2 M aqueous NaOH (10 mL) and EtOAc (25 mL). The organic layer was separated then washed with water (25 mL), brine (25 mL), dried (Na2SO4) and concentrated under reduced pressure to give the title compound 4 as an off white solid (45 mg, 79%); 1H NMR (400 MHz, d4-MeOH) δ 8.79 (dd, J=2.6, 0.5 Hz, 1H), 8.15 (dd, J=8.6, 2.7 Hz, 1H), 8.13 (d, J=0.6 Hz, 1H), 7.28-7.22 (m, 2H), 7.21-7.14 (m, 3H), 3.64 (s, 2H), 3.20-3.10 (m, 4H), 3.02-2.95 (m, 2H), 2.88-2.68 (m, 3H), 2.11 (s, 3H), 1.95-1.84 (m, 2H), 1.71 (qd, J=12.7, 4.0 Hz, 2H). LCMS-A: rt 4.241 min; m/z 431 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-d448f623121549b0b1185d502610759d
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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