Triethylamine → HCID 59532414, compound

HRID 2424632Notes

Reaction equation

HRID 2424632 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].[Cl:24][C:25]1[CH:30]=[CH:29][C:28]([S:31](Cl)(=[O:33])=[O:32])=[CH:27][N:26]=1.C(N(CC)CC)C>C(Cl)Cl>[Cl:24][C:25]1[N:26]=[CH:27][C:28]([S:31]([N:15]([CH3:16])[C:12]2[CH:13]=[CH:14][C:9]([CH2:8][N:6]3[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]3)=[CH:10][CH:11]=2)(=[O:33])=[O:32])=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27927922-Chloro-5-pyridinesulfonyl chlorideHCID 592621311,1-Dimethylethyl (2S)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate

Product 1

HCID 59532414HCID 59532414, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

D3 (500 mg, 1.57 mmol) and 2-chloro-pyridine-5-sulfonyl chloride (330 mg, 1.57 mmol) were combined in DCM (10 mL) under Ar. Triethylamine (0.44 mL, 3.13 mmol) was added and the solution stirred overnight. The solution was diluted with DCM and washed with water. The water layer was re-extracted with DCM. The combined organic layers were washed with brine, dried and concentrated. The crude product was purified by column chromatography. Elution with 0-50% Et2O/petroleum ether yielded the product as a white foam (685 mg), δH (CDCl3, 400 MHz): 1.24 (3H, d), 1.46 (9H, s), 2.01 (1H, m), 2.16 (1H, m), 2.56 (1H, d), 2.73 (1H, d), 3.10 (1H, m), 3.22 (3H, s), 3.40-3.50 (2H, AB), 3.81 (1H, d), 4.20 (1H, br.s), 7.05 (2H, d), 7.31 (2H, d), 7.42 (1H, d), 7.74 (1H, dd), 8.54 (1H, d). MS (ES+): MH+ 495.1/497.1

Workup

  1. washwashed with water
  2. extractionThe water layer was re-extracted with DCM
  3. washThe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated
  6. customThe crude product was purified by column chromatography
  7. washElution with 0-50% Et2O/petroleum ether

Sources & evidence

ORD record
ord-56154e1dcb264f0295dd67099f3f99a1
Source dataset
uspto-grants-2011_06
Patent number
US07964597B2

Reaction notes

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