Diisopropylethylamine → HCID 71208298, compound

HRID 1622249Notes

Reaction equation

HRID 1622249 reaction equation
C(N(C(C)C)C(C)C)C.Cl[C:11]1[N:16]=[CH:15][C:14]([CH2:17][CH3:18])=[CH:13][N:12]=1.C[O:20][C:21](=[O:43])[C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:29]=[CH:30][C:31]3[O:35][CH:34]([CH:36]4[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]4)[CH2:33][C:32]=3[CH:42]=2)=[CH:24][CH:23]=1>O1CCCC1>[CH2:17]([C:14]1[CH:13]=[N:12][C:11]([N:39]2[CH2:40][CH2:41][CH:36]([CH:34]3[CH2:33][C:32]4[CH:42]=[C:28]([C:25]5[CH:24]=[CH:23][C:22]([C:21]([OH:43])=[O:20])=[CH:27][CH:26]=5)[CH:29]=[CH:30][C:31]=4[O:35]3)[CH2:37][CH2:38]2)=[N:16][CH:15]=1)[CH3:18]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 35727632-Chloro-5-ethylpyrimidineHCID 71208354HCID 71208354, compound

Product 1

HCID 71208298HCID 71208298, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyldiisopropylamine (1.38 mL) and 2-chloro-5-ethylpyrimidine (380 μL) are added to a solution of 4-(2-piperidin-4-yl-2,3-dihydro-benzofuran-5-yl)-benzoic acid methyl ester (0.90 g) in tetrahydrofuran (20 mL) and the reaction mixture is heated to reflux for 48 h. The solvent is evaporated after cooling to room temperature. Dichloromethane and water are added; the aqueous phase is separated and extracted with dichloromethane. The combined organic phases are dried over MgSO4 and the solvent is evaporated. The residue is mixed with methanol (20 mL) and 1 M aqueous sodium hydroxide solution (6.67 mL). The reaction mixture is stirred at 55° C. for 12 h. The solvent is evaporated after cooling to room temperature. Dichloromethane and water are added; the organic phase is separated and extracted with water. The combined aqueous phases were adjusted to pH 2 with 1 M hydrochloric acid. The title compound is collected by filtration and dried at 50° C. in vacuo. LC (method 8): tR=1.56 min; Mass spectrum (ESI+): m/z=430 [M+H]+.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureto reflux for 48 h
  3. customThe solvent is evaporated
  4. additionDichloromethane and water are added
  5. customthe aqueous phase is separated
  6. extractionextracted with dichloromethane
  7. dry with materialThe combined organic phases are dried over MgSO4
  8. customthe solvent is evaporated
  9. additionThe residue is mixed with methanol (20 mL) and 1 M aqueous sodium hydroxide solution (6.67 mL)
  10. customThe solvent is evaporated
  11. temperatureafter cooling to room temperature
  12. additionDichloromethane and water are added
  13. customthe organic phase is separated
  14. extractionextracted with water
  15. filtrationThe title compound is collected by filtration
  16. customdried at 50° C. in vacuo

Sources & evidence

ORD record
ord-b490fec908e045768ebc8a948eb98b7d
Source dataset
uspto-grants-2014_07
Patent number
US08778926B2

Reaction notes

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