HCID 178461967, compound → HCID 178461935, compound

HRID 243429Notes

Reaction equation

HRID 243429 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=S)[C@@H:10]([NH:12][C:13]2[N:21]=[CH:20][N:19]=[C:18]3[C:14]=2[N:15]=[CH:16][NH:17]3)[CH3:11])=[C:4]([NH:23][C:24]2[CH:29]=[CH:28][N:27]=[CH:26][N:25]=2)[CH:3]=1>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]2[N:8]=[C:9]([C@@H:10]([NH:12][C:13]3[N:21]=[CH:20][N:19]=[C:18]4[C:14]=3[N:15]=[CH:16][NH:17]4)[CH3:11])[N:23]([C:24]3[CH:29]=[CH:28][N:27]=[CH:26][N:25]=3)[C:4]=2[CH:3]=1

Participants

3

Reactant 1

HCID 178461967HCID 178461967, compound

Product 1

HCID 178461935HCID 178461935, compoundYield 93.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(S)—N-[4-Fluoro-2-(pyrimidin-4-ylamino)phenyl]-2-(9H-purin-6-ylamino)thiopropionamide (9 mg, 0.02 mmol) was heated in toluene at reflux under nitrogen for 15 h. The reaction mixture was purified by column chromatography (Si—PCC, gradient 0-10% (9:1 MeOH/0.880 NH3) in DCM). Product containing fractions were evaporated and freeze dried to give 332 as a colourless solid, (7 mg, 85%). LCMS (Method C): RT 2.82 min [M+H]+ 376.02 1H NMR (DMSO-d6) δ: 12.8 (1H, bs), 9.20 (1H, s), 8.95 (1H, d, J=5.41 Hz), 8.01-7.89 (4H, m), 7.73 (1H, dd, J=8.81, 4.94 Hz), 7.46 (1H, dd, J=9.30, 2.50 Hz), 7.18 (1H, td, J=9.27, 2.48 Hz), 6.03 (1H, bs), 1.71 (3H, d, J=6.78 Hz)

Workup

  1. temperatureat reflux under nitrogen for 15 h
  2. customThe reaction mixture was purified by column chromatography (Si—PCC, gradient 0-10% (9:1 MeOH/0.880 NH3) in DCM)
  3. additionProduct containing fractions
  4. customwere evaporated
  5. customfreeze dried

Sources & evidence

ORD record
ord-e677a9b353c04ecba0f06d2543d3a3dc
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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