Triethylamine → CID 49843530

HRID 1618116Notes

Reaction equation

HRID 1618116 reaction equation
[CH:1]1([N:7]2[CH2:12][CH2:11][CH:10]([N:13]3[C:21](=[O:22])[C:20]4[C:19]([C:23](O)=[O:24])=[CH:18][CH:17]=[CH:16][C:15]=4[C@@H:14]3[CH3:26])[CH2:9][CH2:8]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH4+].OC1C2N=N[NH:34]C=2C=CC=1.C(N(CC)CC)C>O1CCCC1>[CH:1]1([N:7]2[CH2:8][CH2:9][CH:10]([N:13]3[C:21](=[O:22])[C:20]4[C:19]([C:23]([NH2:34])=[O:24])=[CH:18][CH:17]=[CH:16][C:15]=4[C@@H:14]3[CH3:26])[CH2:11][CH2:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 67191867(1S)-2-(1-Cyclohexylpiperidin-4-yl)-1-methyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acidHCID 178515910HCID 178515910, compound

Product 1

HCID 49843530CID 49843530Yield 40.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(1S)-2-(1-Cyclohexylpiperidin-4-yl)-1-methyl-3-oxo-2,3-dihydro-1H-isoindole-4-carboxylic acid (0.15 gr, 0.42 mmol), hydroxybenzotriazole ammonium salt (0.13 gr, 0.84 mmol) and 1-ethyl-3-(3′-dimethylamino) carbodiimide hydrochloric acid salt (0.16 gr, 0.84 mmol) were dissolved in a mixture of tetrahydrofuran (6 mL) and triethylamine (0.23 mL, 1.68 mmol) and stirred under nitrogen atmosphere for 16 hours. Volatiles were evaporated and the crude was dissolved in dichloromethane and washed with 15% ammonium hydroxide. The organic phase was dried over anhydrous sodium sulfate and concentrated in vacuo. The crude was purified by flash chromatography (dichloromethane/methanol/7N ammonia in methanol 100:3:1) to afford the title compound (0.060 g, 40%) as a white solid.

Workup

  1. customVolatiles were evaporated
  2. dissolutionthe crude was dissolved in dichloromethane
  3. washwashed with 15% ammonium hydroxide
  4. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude was purified by flash chromatography (dichloromethane/methanol/7N ammonia in methanol 100:3:1)

Sources & evidence

ORD record
ord-5e3f0c81e928431dad67a5939a76e775
Source dataset
uspto-grants-2014_07
Patent number
US08765972B2

Reaction notes

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