Triethylamine → HCID 21934638, compound

HRID 1241432Notes

Reaction equation

HRID 1241432 reaction equation
[CH:1]([NH:4][C:5](=[O:13])[CH2:6][N:7]1[CH2:12][CH2:11][NH:10][CH2:9][CH2:8]1)([CH3:3])[CH3:2].Cl[C:15]1[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22]2[S:23][CH:24]=[CH:25][N:26]=2)[CH:16]=1.C(N(CC)CC)C.[NH4+].[OH-]>C(O)CCC.CO.C(Cl)Cl>[CH:1]([NH:4][C:5](=[O:13])[CH2:6][N:7]1[CH2:12][CH2:11][N:10]([C:15]2[CH:16]=[C:17]([NH:21][C:22]3[S:23][CH:24]=[CH:25][N:26]=3)[N:18]=[CH:19][N:20]=2)[CH2:9][CH2:8]1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 100826N-isopropyl-1-piperazineacetamideHCID 21934641HCID 21934641, compound

Product 1

HCID 21934638HCID 21934638, compound

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

N-isopropyl-2-piperazin-1-ylacetamide 13-1 (0.74 g, 4.0 mmol)) was suspended in n-butanol to which compound 52-2 (0.85 g, 4.0 mmol) and triethylamine (1.22 g, 12.0 mmol) were added and then heated at 150° C. for 6 hours. The reaction was cooled to room temperature and the precipitate was filtered off, washed with n-butanol and ethyl ether and dried to produce 52-3. Rf=0.45 (DCM:MeOH:NH4OH, 95:5:0.5). 1H-NMR (DMSO-d6): 11.16(s, 1H); 8.33(s, 1H); 7.54(d, 1H); 7.36(s, 1H); 7.05(s, 1H); 6.24(s, 1H); 3.90(m, 1H); 3.55(br s, 4H); 2.94(s, 2H); 2.49(br s, 4H); 1.08(d, 6H).

Workup

  1. additionwere added
  2. temperatureThe reaction was cooled to room temperature
  3. filtrationthe precipitate was filtered off
  4. washwashed with n-butanol and ethyl ether
  5. customdried
  6. customto produce 52-3

Sources & evidence

ORD record
ord-a77de9e0c09442c38965b91e6a197124
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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