Trifluoroacetic acid → HCID 58292921, compound

HRID 511323Notes

Reaction equation

HRID 511323 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=2[C:11]([NH:13][CH3:14])=[O:12])[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=1.[NH2:23][C:24]1[C:38]([O:39][CH3:40])=[CH:37][C:27]([CH2:28][P:29](=[O:36])([O:33][CH2:34][CH3:35])[O:30][CH2:31][CH3:32])=[C:26]([F:41])[CH:25]=1.C(O)(C(F)(F)F)=O>>[F:41][C:26]1[CH:25]=[C:24]([NH:23][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:18]=[CH:17][CH:16]=[CH:15][C:10]=3[C:11](=[O:12])[NH:13][CH3:14])[C:5]([C:19]([F:22])([F:21])[F:20])=[CH:4][N:3]=2)[C:38]([O:39][CH3:40])=[CH:37][C:27]=1[CH2:28][P:29](=[O:36])([O:30][CH2:31][CH3:32])[O:33][CH2:34][CH3:35]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 866338612-((2-Chloro-5-(trifluoromethyl)pyrimidin-4-yl)amino)-N-methylbenzamide2×HCID 86654020HCID 86654020, compound2×

Product 1

HCID 58292921HCID 58292921, compoundYield 54%

Procedure

A solution of 2-{[2-chloro-5-(trifluoromethyl)pyrimidin-4-yl]amino}-N-methylbenzamide (Compound 104A, 75.0 mg, 0.227 mmol) and diethyl (4-amino-2-fluoro-5-methoxybenzyl)phosphonate (Compound 130A, 79.0 mg, 0.271 mmol) in TFE (1.1 mL) was charged with TFA (77.3 mg, 0.678 mmol). The reaction mixture was irradiated on the microwave at 105° C. for 30 min. The reaction mixture was concentrated under reduced pressure to yield a yellow oil. The reaction was purified by silica gel chromatography on the combi-flash Rf system using EtOAc/MeOH (100:0→95:5) as eluent. The fractions containing product were combined and concentrated under reduced pressure to yield a white solid, 71.3 mg (54% yield). 1H NMR (DMSO-d6, 400 MHz): δ=1.20 (t, J=7.07 Hz, 6 H), 2.77 (d, J=4.55 Hz, 3 H), 3.16-3.25 (m, 2 H), 3.79 (s, 3 H), 3.95-4.04 (m, 4 H), 7.01 (d, J=5.05 Hz, 1 H), 7.10-7.17 (m, 1 H), 7.42 (t, J=7.58 Hz, 1 H), 7.70 (d, J=7.58 Hz, 2 H), 8.40 (br. s., 1 H), 8.44 (s, 1 H), 8.67 (s, 1 H), 8.73 (d, J=3.79 Hz, 1 H), 11.41 (s, 1 H). MS (ES+): m/z 586.19 [MH+] (TOF, polar).

Workup

  1. customThe reaction mixture was irradiated on the microwave at 105° C. for 30 min
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customto yield a yellow oil
  4. customThe reaction was purified by silica gel chromatography on the combi-flash Rf system
  5. additionThe fractions containing product
  6. concentrationconcentrated under reduced pressure
  7. customto yield a white solid, 71.3 mg (54% yield)

Sources & evidence

ORD record
ord-36ac1d3ff18849c5a427920a19b0e297
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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