Ethanol → HCID 135830910, compound

HRID 1826269Notes

Reaction equation

HRID 1826269 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([NH:19][C:20]3[CH:25]=[C:24]([O:26][CH3:27])[CH:23]=[CH:22][C:21]=3[Cl:28])=[N:14][CH:15]=[N:16]2)=[C:11]([O:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[CH:10]=1)C1C=CC=CC=1.C(O)C.[H][H]>[Pd].C1COCC1>[Cl:28][C:21]1[CH:22]=[CH:23][C:24]([O:26][CH3:27])=[CH:25][C:20]=1[NH:19][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[CH:10][C:11]=2[O:29][CH2:30][CH2:31][CH2:32][N:33]2[CH2:34][CH2:35][CH2:36][CH2:37]2)[N:16]=[CH:15][N:14]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 22140776HCID 22140776, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135830910HCID 135830910, compoundYield 72.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-benzyloxy-4-(2-chloro-5-methoxyanilino)-5-(3-pyrrolidin-1-ylpropoxy)quinazoline (0.68 g), 10% palladium on charcoal catalyst (0.16 g), ethanol (13 ml) and THF (13 ml) was stirred under 5 atmospheres pressure of hydrogen for 16 hours. The mixture was filtered and the filtrate was evaporated, The residue was triturated under methanol. The resultant solid was isolated, washed with diethyl ether and dried under vacuum. There was thus obtained the title compound (0.405 g); NMR Spectrum: (DMSOd6) 1.65 (br s, 4H), 2.1 (m, 2H), 2.4 (br s, 4H), 2.55 (t, 2H), 3.8 (s, 3H), 4.4 (t, 2H), 6.7 (m, 2H), 6.75 (m, 1H), 7.48 (d, 1H), 8.3 (d, 1H), 8.4 (s, 1H), 10.05 (s, 1H).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated
  3. customThe residue was triturated under methanol
  4. customThe resultant solid was isolated
  5. washwashed with diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-1566ccf41e434be8957e724e19d2923c
Source dataset
uspto-grants-2006_05
Patent number
US07049438B2

Reaction notes

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