Trifluoroacetic acid → HCID 73054607, compound

HRID 1779019Notes

Reaction equation

HRID 1779019 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:28]=[CH:27][C:26]([CH:29]3[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]3)=[CH:25][CH:24]=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]=[CH: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 86712671HCID 86712671, compound

Product 1

HCID 73054607HCID 73054607, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.37 mL, 4.8 mmol) was added to a solution of tert-butyl 4-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)phenyl)piperidine-1-carboxylate (A56) (64 mg, 0.12 mmol) in DCM (20 mL) under nitrogen and the resulting mixture stirred for 24 hours at room temperature. The volatiles were removed in vacuo and the residue was taken up in MeOH and loaded onto an SCX cartridge (10 g). The column was eluted with 5 column volumes of MeOH and then 5 column volumes of 5% v/v aqueous ammonia in MeOH. The volatiles from the ammoniacal filtrate were evaporated under reduced pressure and the resulting solid dried under high vacuum to give the title compound 16 as a white solid (36 mg, 69%); 1H NMR (400 MHz, d6-DMSO) δ 9.28 (s, 1H), 8.15 (s, 1H), 7.67 (d, J=8.6 Hz, 2H), 7.44 (s, 1H), 7.25-7.13 (m, 4H), 7.10 (d, J=8.6 Hz, 2H), 6.93 (s, 1H), 3.50 (s, 2H), 3.10-2.98 (m, 4H), 2.94-2.82 (m, 2H), 2.65-2.53 (m, 3H), 2.06 (s, 3H), 1.67 (d, J=10.6 Hz, 2H), 1.49 (qd, J=12.4, 3.7 Hz, 2H). LCMS-A: rt 4.463 min; m/z 430 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. washThe column was eluted with 5 column volumes of MeOH
  3. customThe volatiles from the ammoniacal filtrate were evaporated under reduced pressure
  4. customthe resulting solid dried under high vacuum

Sources & evidence

ORD record
ord-eb4b5fe9dc6b4312b8f3ef638b225d70
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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