Triethylamine → HCID 10134070, compound

HRID 1937453Notes

Reaction equation

HRID 1937453 reaction equation
[CH:1]1([N:7]=[C:8]=[S:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH:10]1[CH2:14][CH2:13][CH2:12][C@H:11]1[C:15]([O:17][CH2:18][CH2:19][CH2:20][C:21]1[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=1)=[O:16].C(N(CC)CC)C>C(Cl)Cl>[CH:1]1([NH:7][C:8]([N:10]2[CH2:14][CH2:13][CH2:12][C@H:11]2[C:15]([O:17][CH2:18][CH2:19][CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[O:16])=[S:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 14289Cyclohexyl isothiocyanateHCID 15427667HCID 15427667, compound

Product 1

HCID 10134070HCID 10134070, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of cyclohexylisothiocyanate (120 mg; 0.9 mmol), 3-(3-pyridyl)-1-propyl (2S)-pyrrolidine-2-carboxylate (200 mg; 0.9 mmol) triethylamine (90 mg; 0.9 mmol) in 20 mL of methylene chloride was stirred for 1 hour and then partitioned between water and a 1:1 mixture of ethyl acetate and hexane. The organic phase was dried, concentrated and purified by column chromatography (50% ethyl acetate/hexane) to obtain 160 mg (47%) of the compound of Example 3 (Compound 3, Table I). 1H NMR (CDCl3, 300 MHz) δ1.16-1.40 (m, 6H); 1.50-1.71 (m, 4H); 1.95-2.08 (m,7H); 2.70-2.75 (t, 2H); 3.40-3.60 (m, 2H); 4.17-4.26 (m, 2H); 4.95-4.98 (d, 1H); 5.26-5.29 (d, 1H); 7.17-7.25 (m, 1H). Analysis calculated for C20H29N3O2S: C, 63.97; H, 7.78; N, 11.19. Found: C, 63.25; H, 7.80; N, 11.07.

Workup

  1. custompartitioned between water
  2. additiona 1:1 mixture of ethyl acetate and hexane
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. custompurified by column chromatography (50% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-d99964116412449a80b8da4e462f3e6e
Source dataset
uspto-grants-2002_05
Patent number
US06395758B1

Reaction notes

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