5-Methoxyindoleacetic acid → HCID 69337816, compound

HRID 1179087Notes

Reaction equation

HRID 1179087 reaction equation
[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([NH2:9])[CH2:5][CH2:4]1.[Cl-:17].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1.[CH3:35][O:36][C:37]1[CH:38]=[C:39]2[C:43](=[CH:44][CH:45]=1)[NH:42][CH:41]=[C:40]2[CH2:46][C:47](O)=[O:48]>CO>[ClH:17].[CH3:1][N:2]([CH3:16])[C:3]1([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:8][CH2:7][CH:6]([NH:9][C:47](=[O:48])[CH2:46][C:40]2[C:39]3[C:43](=[CH:44][CH:45]=[C:37]([O:36][CH3:35])[CH:38]=3)[NH:42][CH:41]=2)[CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 189865-Methoxyindoleacetic acidHCID 27340594-(4,6-Dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chlorideHCID 129862564-Dimethylamino-4-phenyl-cyclohexylamine

Product 1

HCID 69337816HCID 69337816, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The nonpolar diastereomer of N,N-dimethyl-1-phenyl-cyclohexane-1,4-diamine (387 mg) and 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methyl-morpholinium chloride (267 mg, 2.0 mmol.) were added to a solution of (5-methoxy-1H-indol-3-yl)acetic acid (364 mg) in abs. methanol (20 ml). Stirring was then carried out for 24 hours at RT. For working up, the mixture was concentrated, the batch was diluted with water (10 ml), and the mixture was adjusted to pH 11 with 5M NaOH and extracted with ethyl acetate (3×20 ml). The combined organic extracts were dried over Na2SO4 and concentrated by evaporation. After column chromatography with MeOH, the nonpolar amide (154 mg; colorless oil) was dissolved in 2-butanone (5 ml) and converted with chlorotrimethylsilane (72 μl) into the corresponding hydrochloride (white solid; 168 mg; m.p. 143-145° C.).

Workup

  1. concentrationthe mixture was concentrated
  2. additionthe batch was diluted with water (10 ml)
  3. extractionextracted with ethyl acetate (3×20 ml)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated by evaporation
  6. dissolutionAfter column chromatography with MeOH, the nonpolar amide (154 mg; colorless oil) was dissolved in 2-butanone (5 ml)

Sources & evidence

ORD record
ord-6115a2a4acf54ec8a02ad6aba023be8f
Source dataset
uspto-grants-2007_10
Patent number
US07276518B2

Reaction notes

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