Acetic Acid → HCID 10161646, compound

HRID 2180983Notes

Reaction equation

HRID 2180983 reaction equation
[C:1]([OH:4])(=O)[CH3:2].C1(N=C=NC2CCCCC2)CCCCC1.[NH2:20][CH2:21]/[CH:22]=[CH:23]/[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[N:30]=[CH:29][N:28]=[C:27]2[NH:34][C:35]1[CH:40]=[CH:39][C:38]([O:41][C:42]2[CH:43]=[N:44][C:45]([CH3:48])=[CH:46][CH:47]=2)=[C:37]([Cl:49])[CH:36]=1>C(Cl)Cl>[Cl:49][C:37]1[CH:36]=[C:35]([NH:34][C:27]2[C:26]3[C:31](=[CH:32][CH:33]=[C:24](/[CH:23]=[CH:22]/[CH2:21][NH:20][C:1](=[O:4])[CH3:2])[CH:25]=3)[N:30]=[CH:29][N:28]=2)[CH:40]=[CH:39][C:38]=1[O:41][C:42]1[CH:43]=[N:44][C:45]([CH3:48])=[CH:46][CH:47]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 22484362HCID 22484362, compound

Product 1

HCID 10161646HCID 10161646, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 14.4 μL (0.25 mmol) of acetic acid and 40.3 mg (0.33 mmol) of dicyclohexylcarbodiimide in 2 mL of methylene chloride were stirred for 10 minutes and treated with 100.3 mg of E-[6-(3-amino-propenyl)-quinazolin-4-yl]-[3-chloro-4-(6-methyl-pyridin-3-yloxy)-phenyl]-amine. The reaction was allowed to stir at room temperature overnight. The precipitate which formed was filtered and chromatographed on silica gel, eluting with 6-10% methanol/chloroform to afford 106 mg of the title compound; mp 254-256° C.; 1H NMR (d6 DMSO): δ 9.88 (s, 1), 8.58 (s, 1), 8.48 (m, 1), 8.20 (m, 3), 7.95 (m, 1), 7.83 (m, 1), 7.71(d, J=8.7 Hz, 1), 7.24 (m, 2), 7.19 (d, J=8.7 Hz, 1), 6.61 (d, J=16.2 Hz, 1), 6.48 (m, 1), 3.90 (m, 2).

Workup

  1. stirringto stir at room temperature overnight
  2. customThe precipitate which formed
  3. filtrationwas filtered
  4. customchromatographed on silica gel
  5. washeluting with 6-10% methanol/chloroform

Sources & evidence

ORD record
ord-4bb3b87395064433a70c6a9cc4413e44
Source dataset
uspto-grants-2005_05
Patent number
US06890924B2

Reaction notes

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