4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → n-[(4-Dimethylamino-4-phenylcyclohexylcarbamoyl)methyl]-3-(1h-indol-3-yl)butyramide

HRID 1394238Notes

Reaction equation

HRID 1394238 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][CH:6]1[CH2:11][CH2:10][C:9]([N:18]([CH3:20])[CH3:19])([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH2:7]1)=[O:4].[Cl-].C[O:23]C1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[NH:39]1[C:47]2[C:42](=[CH:43][CH:44]=[CH:45][CH:46]=2)[C:41]([CH:48]([CH2:52][CH3:53])[C:49](O)=O)=[CH:40]1>CO>[CH3:19][N:18]([CH3:20])[C:9]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:10][CH2:11][CH:6]([NH:5][C:3]([CH2:2][NH:1][C:53](=[O:23])[CH2:52][CH:48]([C:41]2[C:42]3[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=3)[NH:39][CH:40]=2)[CH3:49])=[O:4])[CH2:7][CH2:8]1

Participants

5

Reactant 3

HCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 122300802-(1H-indol-3-yl)butanoic acidHCID 692169152-Amino-n-(4-dimethylamino-4-phenylcyclohexyl)acetamide

Product 1

HCID 69216438n-[(4-Dimethylamino-4-phenylcyclohexylcarbamoyl)methyl]-3-(1h-indol-3-yl)butyramide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The more nonpolar diastereomer of 2-amino-N-(4-dimethylamino-4-phenylcyclohexyl)acetamide (276 mg, 1.0 mmole) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (415 mg, 1.5 mmole) were added to a solution of indol-3-yl-butyric acid (203 mg, 1.0 mmole) in MeOH and stirred for 24 h at room temperature. Working up was performed by removing MeOH by distillation. The batch was re-dissolved with water, adjusted to pH 11 with 5M NaOH and extracted with ethyl acetate. The organic phase was dried with Na2SO4 and evaporated. The more nonpolar amide was obtained as a colorless oil in a yield of 450 mg (98%).

Workup

  1. customby removing MeOH
  2. distillationby distillation
  3. dissolutionThe batch was re-dissolved with water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic phase was dried with Na2SO4
  6. customevaporated

Sources & evidence

ORD record
ord-7953475dcd6b47b8b464e0048a0943cc
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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