Triethylamine → HCID 59532403, compound

HRID 2424634Notes

Reaction equation

HRID 2424634 reaction equation
[CH3:1][C@H:2]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([NH:15][CH3:16])=[CH:11][CH:10]=2)[CH2:5][CH2:4][N:3]1[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(N(CC)CC)C.[F:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([S:44](Cl)(=[O:46])=[O:45])=[CH:40][CH:39]=2)=[CH:34][CH:33]=1>C(Cl)Cl>[F:31][C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([S:44]([N:15]([CH3:16])[C:12]3[CH:13]=[CH:14][C:9]([CH2:8][N:6]4[CH2:5][CH2:4][N:3]([C:17]([O:19][C:20]([CH3:22])([CH3:21])[CH3:23])=[O:18])[C@@H:2]([CH3:1])[CH2:7]4)=[CH:10][CH:11]=3)(=[O:46])=[O:45])=[CH:40][CH:39]=2)=[CH:34][CH:33]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27947494'-Fluorobiphenyl-4-sulfonyl chlorideHCID 592621311,1-Dimethylethyl (2S)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate

Product 1

HCID 59532403HCID 59532403, compoundYield 30.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

D3 (100 mg, 0.31 mmol) and triethylamine (65 ul, 0.47 mmol) were combined in dry DCM (3 mL) under argon. 4′-Fluoro-4-biphenylsulfonyl chloride (93 mg, 0.34 mmol) was added dropwise in a solution of dry DCM (3 mL). The reaction mixture was stirred at room temperature under argon for 19 h and diluted with DCM (20 mL) and washed with water then the organic layer was dried (Na2SO4) and concentrated in vacuo. The crude material was purified by chromatography eluting with 0-100% Et2O/petroleum ether to afford the title compound (53 mg), δH (CDCl3), 400 MHz: 1.23 (3H, d), 1.46 (9H, s), 2.01 (1H, m), 2.14, 1H, dd), 2.57 (1H, m), 2.74 (1H, m), 3.10 (1H, m), 3.21 (3H, s), 3.39-3.51 (2H, AB), 3.81 (1H, d), 4.19 (1H, br.s), 7.08 (2H, d), 7.17 (2H, t), 7.28 (2H, m), 7.57 (2H, dd), 7.61 (4H, s). MS (ES+): MH+ 554.3

Workup

  1. washwashed with water
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. concentrationconcentrated in vacuo
  4. customThe crude material was purified by chromatography
  5. washeluting with 0-100% Et2O/petroleum ether

Sources & evidence

ORD record
ord-a5756cf4c92841ea902d703078cd2595
Source dataset
uspto-grants-2011_06
Patent number
US07964597B2

Reaction notes

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