1-Pyrrolidinepropanamine → HCID 22594099, compound

HRID 1760965Notes

Reaction equation

HRID 1760965 reaction equation
[CH3:1][N:2]([CH3:27])[C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=1)[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:23])=[C:13]([CH:22]=1)[NH:14][C:15]1[CH:20]=[C:19](Cl)[N:18]=[CH:17][N:16]=1)=[O:7].[N:28]1([CH2:33][CH2:34][CH2:35][NH2:36])[CH2:32][CH2:31][CH2:30][CH2:29]1.C(N(CC)C(C)C)(C)C>C(O)CCC>[CH3:1][N:2]([CH3:27])[C:3]1[CH:4]=[C:5]([CH:24]=[CH:25][CH:26]=1)[C:6]([NH:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:23])=[C:13]([CH:22]=1)[NH:14][C:15]1[CH:20]=[C:19]([NH:36][CH2:35][CH2:34][CH2:33][N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[N:18]=[CH:17][N:16]=1)=[O:7]

Participants

5

Reactant 3

HCID 316701-PyrrolidinepropanamineHCID 81531DiisopropylethylamineHCID 22594113HCID 22594113, compound

Product 1

HCID 22594099HCID 22594099, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 4-[5-(3-dimethylaminobenzamido)-2-methylanilino]-6-chloropyrimidine (0.114 g), 3-pyrrolidin-1-ylpropylamine (0.95 ml), N,N-di-isopropylethylamine (0.063 ml) and n-butanol (2 ml) was stirred and heated to reflux for 18 hours. The mixture was evaporated and the residue was purified by column chromatography on silica using a 10:1 mixture of ethyl acetate and methanol as eluent. There was thus obtained the title compound (0.124 g); NMR Spectrum: (DMSOd6) 1.59 (m, 6H), 2.15 (s, 3H), 2.34 (m, 6H), 2.93 (s, 6H), 3.14 (m, 2H), 6.72 (m, 1H), 6.89 (m, 1H), 7.2 (m, 4H), 7.3 (m, 1H), 7.5 (m, 1H), 7.72 (m, 1H), 7.96 (m, 1H), 8.16 (s, 1H), 10.02 (s, 1H); Mass Spectrum: M+H+ 474.

Workup

  1. temperatureheated
  2. temperatureto reflux for 18 hours
  3. customThe mixture was evaporated
  4. customthe residue was purified by column chromatography on silica using
  5. additiona 10:1 mixture of ethyl acetate and methanol as eluent

Sources & evidence

ORD record
ord-e5cbc5afa82e46fdbb07f13472749b0c
Source dataset
uspto-grants-2005_01
Patent number
US06846827B1

Reaction notes

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