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 1394243Notes

Reaction equation

HRID 1394243 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 polar diastereomer of 2-amino-N-(4-dimethylamino-4-phenylcyclohexyl)-acetamide (159 mg, 0.57 mmole) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (239 mg, 0.86 mmole) were added to a solution of indol-3-yl-hexanoic acid (133 mg, 0.57 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 polar amide was obtained as a colorless oil in a yield of 281 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-882cdf573f4049a0a0a1f7479cf95d9f
Source dataset
uspto-grants-2008_03
Patent number
US07348354B2

Reaction notes

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