Trifluoroacetic acid → 2-(2-(2-(2-((4-(Azetidin-3-yl)phenyl)amino)-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamide

HRID 1779094Notes

Reaction equation

HRID 1779094 reaction equation
C(O)(C(F)(F)F)=O.[NH2:8][C:9](=[O:44])[CH2:10][C:11]1[CH:43]=[CH:42][CH:41]=[CH:40][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[CH2:32][N:31](C(OC(C)(C)C)=O)[CH2:30]3)=[CH:25][CH:24]=2)[N:16]=1>C(Cl)Cl>[NH:31]1[CH2:32][CH:29]([C:26]2[CH:25]=[CH:24][C:23]([NH:22][C:17]3[N:16]=[C:15]([CH2:14][CH2:13][C:12]4[CH:40]=[CH:41][CH:42]=[CH:43][C:11]=4[CH2:10][C:9]([NH2:8])=[O:44])[C:20]([CH3:21])=[CH:19][N:18]=3)=[CH:28][CH:27]=2)[CH2:30]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86712728tert-Butyl 3-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate

Product 1

HCID 730560402-(2-(2-(2-((4-(Azetidin-3-yl)phenyl)amino)-5-methylpyrimidin-4-yl)ethyl)phenyl)acetamideYield 11.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (1 mL) was added to a solution of tert-butyl 3-(4-((4-(2-(2-amino-2-oxoethyl)phenethyl)-5-methylpyrimidin-2-yl)amino)phenyl)azetidine-1-carboxylate (A123) (0.087 g, 0.17 mmol) in DCM (3 mL) and the resulting mixture stirred at room temperature for 3 hours. The volatiles were removed in vacuo then 2 M aqueous K2CO3 solution (5 mL) and water (15 mL) were added to the residue. The resulting suspension was sonicated for 1 minute, filtered and the filter cake dried. The resulting residue was purified by semi preparative HPLC to give the title compound 32 as a light tan solid (7.6 mg, 10%); 1H NMR (300 MHz, d4-MeOH) δ 8.12 (s, 1H), 7.74 (d, J=8.6 Hz, 2H), 7.33 (d, J=8.6 Hz, 2H), 7.18-7.28 (m, 4H), 4.31-4.39 (m, 2H), 4.19-4.27 (m, 3H), 3.66 (s, 2H), 3.13-3.18 (m, 2H), 2.96-3.01 (m, 2H), 2.12 (s, 3H). LCMS-B: rt 4.725 min; m/z 402 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. addition2 M aqueous K2CO3 solution (5 mL) and water (15 mL) were added to the residue
  3. customThe resulting suspension was sonicated for 1 minute
  4. filtrationfiltered
  5. customthe filter cake dried
  6. customThe resulting residue was purified by semi preparative HPLC

Sources & evidence

ORD record
ord-337c4762b4b446b8b023d85d24cb4470
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

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