Diisopropylethylamine → HCID 67383963, compound

HRID 1958350Notes

Reaction equation

HRID 1958350 reaction equation
[F:1][CH2:2][O:3][C:4]1[CH:5]=[C:6]([C:10]2[N:11]=[C:12]3[CH:17]=[C:16]([NH2:18])[N:15]=[CH:14][N:13]3[CH:19]=2)[CH:7]=[CH:8][CH:9]=1.[N:20]1([C:24]([C:26]2[CH:27]=[N:28][N:29]([CH3:34])[C:30]=2[C:31](O)=[O:32])=[O:25])[CH2:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C.C([O-])(O)=O.[Na+]>CCOC(C)=O>[N:20]1([C:24]([C:26]2[CH:27]=[N:28][N:29]([CH3:34])[C:30]=2[C:31]([NH:18][C:16]2[CH:17]=[CH:12][N:13]3[CH:19]=[C:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([O:3][CH2:2][F:1])[CH:5]=4)[N:11]=[C:14]3[N:15]=2)=[O:32])=[O:25])[CH2:21][CH2:22][CH2:23]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 58446922HCID 58446922, compoundHCID 67391916HCID 67391916, compound

Product 1

HCID 67383963HCID 67383963, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

2-(3-Fluoromethoxy-phenyl)-imidazo[1,2-c]pyrimidin-7-ylamine (100 mg, 0.387 μmol) was combined with EtOAc (2.0 ml) to give a light yellow suspension. 4-(Azetidine-1-carbonyl)-1-methyl-1H-pyrazole-5-carboxylic acid (97 mg, 465 μmol) and DIPEA (300 mg, 406 μl, 2.32 mmol) were added. The reaction mixture was cooled down to 0° C. and n-propylphosphonic acid anhydride, cyclic trimer (616 mg, 582 μl, 968 μmol) was added drop by drop. After stirring at 0° C. for 30 min the reaction mixture was allowed to warm-up and stirred at RT overnight. The reaction mixture was then diluted with and 10% NaHCO3 aq. solution and extracted with EtOAc (3×). The combined organic layers were dried (MgSO4) and concentrated under vacuum. The crude product was purified by flash chromatography (10 g SiO2; eluent: CH2Cl2 to CH2Cl2/MeOH/NH3 140:10:1). The obtain material was dissolved in CH2Cl2 and the product was precipitated with Et2O, filtered off, washed with Et2O, and dried overnight at HV. Yellow solid (89 mg, 47%). MS (m/z)=450.2 [M+H+].

Workup

  1. customto give a light yellow suspension
  2. temperatureto warm-up
  3. stirringstirred at RT overnight
  4. extractionextracted with EtOAc (3×)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customThe crude product was purified by flash chromatography (10 g SiO2; eluent: CH2Cl2 to CH2Cl2/MeOH/NH3 140:10:1)
  8. dissolutionThe obtain material was dissolved in CH2Cl2
  9. customthe product was precipitated with Et2O
  10. filtrationfiltered off
  11. washwashed with Et2O
  12. customdried overnight at HV

Sources & evidence

ORD record
ord-6c21ae34ace544568ed065f8a24e087a
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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