4-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride → 6-(1h-Indol-3-yl)hexanoic acid [(4-dimethylamino-4-phenylcyclohexylcarbamoyl)methyl]amide

HRID 1394242Notes

Reaction equation

HRID 1394242 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-].[CH3:22][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][CH2:53][CH2:54][CH3:55])C(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:22](=[O:23])[CH2:55][CH2:54][CH2:53][CH2:52][CH2:48][C:41]2[C:42]3[C:47](=[CH:46][CH:45]=[CH:44][CH:43]=3)[NH:39][CH:40]=2)=[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 692169152-Amino-n-(4-dimethylamino-4-phenylcyclohexyl)acetamideHCID 69219720Indol-3-yl-hexanoic acid

Product 1

HCID 104819526-(1h-Indol-3-yl)hexanoic acid [(4-dimethylamino-4-phenylcyclohexylcarbamoyl)methyl]amide

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-hexanoic acid (231 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 525 mg (100%).

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-135933e9d4a14cb99be4ea9ef8e88726
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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