Acryloyl chloride → HCID 71721597, compound

HRID 336157Notes

Reaction equation

HRID 336157 reaction equation
C(N(CC)C(C)C)(C)C.[C:10](Cl)(=[O:13])[CH:11]=[CH2:12].[N:15]1[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=[C:17]([C:25]2[C:26]3[C:39]([NH2:40])=[N:38][CH:37]=[N:36][C:27]=3[N:28]3[CH2:34][CH2:33][C@@H:32]([NH2:35])[CH2:31][CH2:30][C:29]=23)[CH:16]=1.C(=O)(O)[O-].[Na+]>C(#N)C.O>[NH2:40][C:39]1[C:26]2[C:25]([C:17]3[CH:16]=[N:15][C:24]4[C:19]([CH:18]=3)=[CH:20][CH:21]=[CH:22][CH:23]=4)=[C:29]3[CH2:30][CH2:31][C@H:32]([NH:35][C:10](=[O:13])[CH:11]=[CH2:12])[CH2:33][CH2:34][N:28]3[C:27]=2[N:36]=[CH:37][N:38]=1

Participants

7

Reactant 4

HCID 13140Acryloyl chlorideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 86711291HCID 86711291, compound

Product 1

HCID 71721597HCID 71721597, compoundYield 61.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×

Procedure

N,N-Diisopropylethylamine (0.192 ml) and a solution of acryloyl chloride (83.3 mg) in acetonitrile (0.83 ml) were added to an acetonitrile (1.6 ml)-water (1.6 ml) solution of the (S)-5-(quinolin-3-yl)-7,8,9,10-tetrahydro-6H-pyrimido[5′,4′:4,5]pyrrolo[1,2-a]azepin-4,8-diamine (317 mg) obtained in Step 9 under ice-cooling. After being stirred at the same temperature for 15 minutes, the mixture was poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with chloroform. The organic layer was dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/methanol) to obtain the title compound as a light-yellow solid (226 mg).

Workup

  1. temperaturecooling
  2. extractionfollowed by extraction with chloroform
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. distillationthe solvent was then distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/methanol)

Sources & evidence

ORD record
ord-450f17c90b8c484c91f886fefa788af4
Source dataset
uspto-grants-2014_11
Patent number
US08889666B2

Reaction notes

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