Diisopropylethylamine → HCID 18784692, compound

HRID 1741093Notes

Reaction equation

HRID 1741093 reaction equation
C[N:2]1[CH2:7][CH2:6][C:5]2([C:18]3[C:10](=[CH:11][C:12]4[CH2:13][CH2:14][N:15]([C:19]([C:21]5[CH:26]=[CH:25][C:24]([C:27]6[CH:32]=[CH:31][C:30]([C:33]7[N:37]=[C:36]([CH3:38])[O:35][N:34]=7)=[CH:29][C:28]=6[CH3:39])=[CH:23][CH:22]=5)=[O:20])[C:16]=4[CH:17]=3)[O:9][CH2:8]2)[CH2:4][CH2:3]1.C(N(C(C)C)CC)(C)C.ClC(OC(Cl)C)=O>ClCCCl>[CH3:39][C:28]1[CH:29]=[C:30]([C:33]2[N:37]=[C:36]([CH3:38])[O:35][N:34]=2)[CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[CH:22][C:21]([C:19]([N:15]2[C:16]3[CH:17]=[C:18]4[C:5]5([CH2:8][O:9][C:10]4=[CH:11][C:12]=3[CH2:13][CH2:14]2)[CH2:4][CH2:3][NH:2][CH2:7][CH2:6]5)=[O:20])=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 5213051-Chloroethyl chloroformate2×HCID 3378093SB 224289

Product 1

HCID 18784692HCID 18784692, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A stirred solution of 1'-methyl-5-(2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carbonyl)-2,3,6,7-tetrahydrospiro[furo[2,3-f]indole-3,4'-piperidine] (E1, 350 mg, 0.67 mmole) in 1,2-dichloroethane (15 ml) under argon was treated with diisopropylethylamine (0.14 ml, 0.80 mmole) and 1-chloroethyl chloroformate (0.09 ml, 0.80 mmole). The mixture was stirred at room temperature for 2 h followed by 1 h at reflux temperature. Additional diisopropylethylamine (0.10 ml, 0.57 mmole) and 1-chloroethyl chloroformate (0.06 ml, 0.53 mmole) was added and reaction maintained at reflux for a further 1 h. The solution was concentrated in vacuo and the residue treated with methanol (20 ml) and heated under reflux for 1 h. The solution was concentrated in vacuo and the residue treated with conc. K2CO3 solution (25 ml) and chloroform (25 ml), shaken well and the chloroform solution separated, dried (Na2SO4) and concentrated in vacuo to afford the title compound as a beige solid (340 mg, 100%). The hydrochloride salt was prepared from acetone/ether as a white solid mp 203-210° C.

Workup

  1. waitfollowed by 1 h
  2. temperatureat reflux temperature
  3. customreaction
  4. temperaturemaintained
  5. temperatureat reflux for a further 1 h
  6. concentrationThe solution was concentrated in vacuo
  7. additionthe residue treated with methanol (20 ml)
  8. temperatureheated
  9. temperatureunder reflux for 1 h
  10. concentrationThe solution was concentrated in vacuo
  11. additionthe residue treated with conc. K2CO3 solution (25 ml) and chloroform (25 ml)
  12. stirringshaken well
  13. customthe chloroform solution separated
  14. dry with materialdried (Na2SO4)
  15. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b996b12cdbff4267b974dd0fd487553a
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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