Tryptamine → HCID 11604571, compound

HRID 908950Notes

Reaction equation

HRID 908950 reaction equation
ON1C2C=CC=CC=2N=N1.[NH2:11][CH2:12][CH2:13][C:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[NH:16][CH:15]=1.CN1CCOCC1.[CH3:30][N:31]([CH3:49])[C:32]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=2)[CH2:37][CH2:36][C:35]([CH2:39][C:40](O)=[O:41])(O)[CH2:34][CH2:33]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>O.CN(C)C=O>[CH3:49][N:31]([CH3:30])[C:32]1([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][N:44]=2)[CH2:37][CH2:36][C:35](=[CH:39][C:40]([NH:11][CH2:12][CH2:13][C:14]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:16][CH:15]=2)=[O:41])[CH2:34][CH2:33]1

Participants

9

Reactant 6

HCID 1150TryptamineHCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 67386014HCID 67386014, compound

Product 1

HCID 11604571HCID 11604571, compoundYield 25%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

1-Hydroxybenzotriazole (546 mg, 4.0 mmol), tryptamine (320 mg, 2.0 mmol) and N-methylmorpholine (0.444 ml, 4.0 mmol) were added to a solution of (4-dimethylamino-1-hydroxy-4-pyridin-2-yl-cyclohexyl)acetic acid (556 mg, 2.0 mmol) in abs. dimethylformamide (30 ml) under argon. The solution was cooled to 0° C., dicyclohexylcarbodiimide (825 mg, 4.0 mmol) was added and the mixture was stirred at RT for 7 d. Working up of the mixture was carried out by separating off the urea which had precipitated out and introducing the filtrate into a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml). Still further urea thereby precipitated out and was separated off. The aqueous phase was diluted with water (400 ml), 5 M sodium hydroxide solution (7 ml, 35 mmol) was added and the mixture was stored at 5° C. for 16 h. The crude product thereby precipitated out as a beige-coloured solid (313 mg, 37%). After chromatography on silica gel (45 g) with EA/methanol (4:1), the product was obtained as a beige-coloured solid in a yield of 25% (210 mg).

Workup

  1. customby separating off the urea which
  2. customhad precipitated out
  3. additionintroducing the filtrate
  4. additioninto a mixture of saturated NaCl solution (40 ml) and saturated NaHCO3 solution (10 ml)
  5. customStill further urea thereby precipitated out and
  6. customwas separated off
  7. additionwas added
  8. waitthe mixture was stored at 5° C. for 16 h
  9. customThe crude product thereby precipitated out as a beige-coloured solid (313 mg, 37%)
  10. customAfter chromatography on silica gel (45 g) with EA/methanol (4:1), the product was obtained as a beige-coloured solid in a yield of 25% (210 mg)

Sources & evidence

ORD record
ord-4ae643a833bf46b6b08798868bfee2b5
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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