Triethylamine → HCID 18665720, compound

HRID 365454Notes

Reaction equation

HRID 365454 reaction equation
Cl.Cl.[C:3]([C:5]1[CH:27]=[CH:26][C:8]([CH2:9][N:10]2[C:14]([CH2:15][CH2:16][NH:17][C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][NH:22][CH2:21]3)=[O:19])=[CH:13][N:12]=[CH:11]2)=[CH:7][CH:6]=1)#[N:4].CCN(CC)CC.[C:35]1([N:41]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:42](Cl)=[O:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C(Cl)Cl>[C:35]1([N:41]([C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)[C:42]([N:22]2[CH2:23][CH2:24][CH2:25][C@H:20]([C:18](=[O:19])[NH:17][CH2:16][CH2:15][C:14]3[N:10]([CH2:9][C:8]4[CH:7]=[CH:6][C:5]([C:3]#[N:4])=[CH:27][CH:26]=4)[CH:11]=[N:12][CH:13]=3)[CH2:21]2)=[O:43])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 65741N,N-Diphenylcarbamic chlorideHCID 18665751HCID 18665751, compound

Product 1

HCID 18665720HCID 18665720, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3(S)-[N-(1-(4-cyanobenzyl)-1H-imidazol-5-ylethyl)carbamoyl]piperidine dihydrochloride (Example 11, Step E) (0.346 g, 0.843 mmol) was dissolved in CH2Cl2 (10 mL), treated with Et3N (0.587 mL, 4.2 mmol) and diphenylcarbamoyl chloride (0.390 g, 1.686 mmol) and stirred at ambient temperature for 1 hr. The reaction mixture was concentrated to dryness, partitioned between EtOAc and satd NaHCO3 soln, the organic layer separated, washed with brine, and dried (MgSO4). Filtration and concentration to dryness gave the title compound after purification on a silica gel column eluting with 0-2% MeOH/CH2Cl2. Anal. calculated for C32H32N6O2.0.95 H2O: C, 69.91; H, 6.22; N, 15.29; Found C, 69.97; H, 6.15; N, 14.80.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. custompartitioned between EtOAc
  3. customthe organic layer separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationFiltration and concentration to dryness

Sources & evidence

ORD record
ord-fe048dc1a82242359b9c02b7ee7b4fe3
Source dataset
uspto-grants-2000_10
Patent number
US06127366

Reaction notes

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