Ethanolamine → HCID 178486733, compound

HRID 890965Notes

Reaction equation

HRID 890965 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([NH:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][CH:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][N:14]=1)=S.[NH2:34][CH2:35][CH2:36][OH:37].C(Cl)(Cl)Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[NH:9][C:10]([NH:34][CH2:35][CH2:36][OH:37])=[N:12][C:13]1[C:22]2[C:17](=[CH:18][C:19]([O:25][CH2:26][CH:27]3[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]3)=[C:20]([O:23][CH3:24])[CH:21]=2)[N:16]=[CH:15][N:14]=1

Participants

5

Reactant 3

HCID 700EthanolamineHCID 6212ChloroformHCID 11213905HCID 11213905, compound

Product 1

HCID 178486733HCID 178486733, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Mercuric(II) oxide (0.107 g) was added to a mixture of 1-(2-chloro-6-methylphenyl)-3-[6-methoxy-7-(N-methylpiperidin-4-ylmethoxy)quinazolin-4-yl]thiourea (0.118 g), 2-aminoethanol (0.03 ml), chloroform (5 ml) and methanol (5 ml) and the resultant mixture was stirred at ambient temperature for 2 hours. The reaction mixture was filtered and the filtrate was evaporated. The residue was purified by column chromatography on silica using increasingly polar mixtures of methylene chloride and a 2M solution of ammonia gas in methanol as eluent. There was thus obtained the title compound (0.128 g); NMR Spectrum: (DMSOd6+CD3CO2D) 1.47–1.62 (m, 2H), 1.85–2.11 (m, 5H), 2.29 (s, 3H), 2.67 (s, 3H), 2.87 (t, 2H), 3.33 (d, 2H), 3.59 (t, 4H), 3.79 (s, 3H), 4.0 (d, 2H), 7.08 (s, 1H), 7.19–7.32 (m, 3H), 7.4 (d, 1H), 8.43 (s, 1H), 10.5 (br s, 1H); Mass Spectrum: M+H+ 513 and 515.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was purified by column chromatography on silica using
  4. temperatureincreasingly polar mixtures of methylene chloride

Sources & evidence

ORD record
ord-6a1fe0f19db5428a9690045e260f8ac0
Source dataset
uspto-grants-2006_02
Patent number
US07001904B1

Reaction notes

Loading…