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

HRID 400531Notes

Reaction equation

HRID 400531 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-41571eec2a8841e08cb570573593d929
Source dataset
uspto-grants-2014_06
Patent number
US08741899B2

Reaction notes

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