4-Methylmorpholine → HCID 11597063, compound

HRID 908970Notes

Reaction equation

HRID 908970 reaction equation
ON1C2C=CC=CC=2N=N1.[NH:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][NH2:21])=[CH:12]1.CN1CCOCC1.Cl.[CH3:30][N:31]([CH3:48])[C:32]1([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:37][CH2:36][CH:35]([CH2:38][C:39](O)=[O:40])[CH2:34][CH2:33]1.C1(N=C=NC2CCCCC2)CCCCC1.[OH-].[Na+]>CN(C)C=O.O>[CH3:48][N:31]([CH3:30])[C:32]1([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:37][CH2:36][CH:35]([CH2:38][C:39]([NH:21][CH2:20][C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[NH:11][CH:12]=2)=[O:40])[CH2:34][CH2:33]1

Participants

9

Reactant 6

HCID 79724-MethylmorpholineHCID 10868DicyclohexylcarbodiimideHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 4721071H-Indol-3-YlmethanamineHCID 673861314-Dimethylamino-4-phenylcyclohexyl-acetic acid hydrochloride

Product 1

HCID 11597063HCID 11597063, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

1-Hydroxybenzotriazole (546 mg, 4.0 mmol), C-(1H-indol-3-yl)methylamine (292 mg, 2.0 mmol) and N-methylmorpholine (0.444 ml, 4.0 mmol) were added to a solution of (4-dimethylamino-4-phenylcyclohexyl)acetic acid hydrochloride (596 mg, 2.0 mmol) in dry dimethylformamide under argon. Dicyclohexylcarbodiimide (834 mg, 4.0 mmol) was added at 0° C. 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). A mixture of urea and product thereby precipitated out (482 mg) and was separated off. The filtrate obtained was diluted with water (300 ml), 5 M sodium hydroxide solution (4 ml, 20 mmol) was added and the mixture was stored at 5° C. for 16 h. A crude product thereby precipitated out as a beige-coloured substance (234 mg), which was separated off by filtration. After purification of the two product fractions by chromatography on silica gel with EA/methanol (4:1) and methanol, the product was isolated as a beige-coloured solid in a yield of 30% (230 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. additionA mixture of urea and product
  6. customthereby precipitated out (482 mg)
  7. customwas separated off
  8. customThe filtrate obtained
  9. additionwas added
  10. waitthe mixture was stored at 5° C. for 16 h
  11. customA crude product thereby precipitated out as a beige-coloured substance (234 mg), which
  12. customwas separated off by filtration
  13. customAfter purification of the two product fractions by chromatography on silica gel with EA/methanol (4:1) and methanol
  14. customthe product was isolated as a beige-coloured solid in a yield of 30% (230 mg)

Sources & evidence

ORD record
ord-03de9e8d32464ec8af48b4a98c42cc87
Source dataset
uspto-grants-2011_09
Patent number
US08017630B2

Reaction notes

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