6-(Pyrimidin-5-YL)hexan-1-amine → (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-N-[6-(5-pyrimidinyl)hexyl]-2-propenamide

HRID 1651253Notes

Reaction equation

HRID 1651253 reaction equation
[N+](C1C=CC([O:10][C:11](=O)/[CH:12]=[CH:13]/[C:14]2[CH:23]=[C:22]([O:24][CH3:25])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]=2[CH2:26][CH2:27][CH2:28][CH3:29])=CC=1)([O-])=O.[N:31]1[CH:36]=[C:35]([CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][NH2:43])[CH:34]=[N:33][CH:32]=1>O1CCCC1>[CH2:26]([C:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:22]([O:24][CH3:25])=[CH:23][C:14]=1/[CH:13]=[CH:12]/[C:11]([NH:43][CH2:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][C:35]1[CH:36]=[N:31][CH:32]=[N:33][CH:34]=1)=[O:10])[CH2:27][CH2:28][CH3:29]

Participants

4

Reactant 2

HCID 135575456-(Pyrimidin-5-YL)hexan-1-amineHCID 14742811(E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid 4-nitrophenyl ester

Product 1

HCID 23051560(E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-N-[6-(5-pyrimidinyl)hexyl]-2-propenamideYield 68.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As in Example 114, (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-2-propenoic acid 4-nitrophenyl ester (1.21 g) was reacted with 5-pyrimidinehexanamine (0.505 g) in tetrahydrofuran (20 mL) at room temperature overnight and then at 50° C. for 1.5 hour. The product was isolated in the usual manner then was purified by HPLC (ethyl acetate) and twice crystallized from ethyl acetate-hexane to provide 0.86 g of (E)-3-(1-butyl-4-methoxy-2-naphthalenyl)-N-[6-(5-pyrimidinyl)hexyl]-2-propenamide, mp 128°-129° C. Anal. Calcd for C28H35N3O2 : C, 75.47; H, 7.92; N, 9.43 Found: C, 75.52; H, 7.95; N, 9.40

Workup

  1. customThe product was isolated in the usual manner
  2. customthen was purified by HPLC (ethyl acetate)
  3. customtwice crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-5553de70a1614784a8ebb88a982aaafa
Source dataset
uspto-grants-1990_05
Patent number
US04927838

Reaction notes

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