1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 46852902, compound

HRID 421788Notes

Reaction equation

HRID 421788 reaction equation
[CH:1]([N:4]([C:18]1[CH:19]=[C:20]([CH:24]=[CH:25][CH:26]=1)[C:21]([OH:23])=O)[S:5]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=1)(=[O:7])=[O:6])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.CN(C)CCCN=C=NCC.[CH2:49]1[NH:54][CH2:53][CH2:52][N:51]2[CH2:55][CH2:56][CH2:57][C@H:50]12>ClCCl.CN(C)C=O.ClCCl>[CH2:49]1[N:54]([C:21]([C:20]2[CH:19]=[C:18]([N:4]([CH:1]([CH3:3])[CH3:2])[S:5]([C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:15])[F:16])[CH:9]=3)(=[O:7])=[O:6])[CH:26]=[CH:25][CH:24]=2)=[O:23])[CH2:53][CH2:52][N:51]2[CH2:55][CH2:56][CH2:57][C@H:50]12

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 7004239(8aR)-Octahydropyrrolo(1,2-a)pyrazineHCID 66676232HCID 66676232, compound

Product 1

HCID 46852902HCID 46852902, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a mixture of 3-(N-isopropyl-3-(trifluoromethyl)phenylsulfonamido)benzoic acid (155 mg, 0.4 mmol) and 1-hydroxybenzotriazole hydrate (61 mg, 0.4 mmol) in dichloromethane/N,N-dimethylformamide (4:1, 6 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (EDC, 62 mg, 0.4 mmol) in dichloromethane (1 mL). After 5 minutes, (R)-octahydropyrrolo[1,2-a]pyrazine (50 mg, 0.4 mmol) in dichloromethane (1 mL) was added. The mixture was stirred at room temperature overnight. Then the mixture was concentrated. The residue was diluted with ethyl acetate (100 mL), washed with water (2×20 mL), dried over sodium sulfate, and concentrated. The residue was purified by chromatography on silica gel (dichloromethane, then methanol/dichloromethane=1:12) to give the titled compound: 1H NMR (300 MHz, DMSO-d6) δ ppm 1.00 (d, 6H, J=8 Hz), 1.35 (m, 1H), 1.65-2.10 (m, 6H), 2.80-3.05 (m, 4H), 3.45-3.55 (m, 1H), 4.40-4.50 (m, 1H), 4.60 (m, 1H), 6.98 (s, 1H), 7.15 (m, 1H), 7.50 (m, 2H), 7.88 (m, 2H), 8.10 (m, 2H); MS (ESI) m/z 496 (M+H)+.

Workup

  1. concentrationThen the mixture was concentrated
  2. additionThe residue was diluted with ethyl acetate (100 mL)
  3. washwashed with water (2×20 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica gel (dichloromethane

Sources & evidence

ORD record
ord-41027878ee214c8cb8e78b61183d1b37
Source dataset
uspto-grants-2012_01
Patent number
US08101614B2

Reaction notes

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