Dichloromethane → 6-Methoxy-4-(2,3-methylenedioxyanilino)-7-(3-methylsulphonylpropoxy)quinazoline monohydrochloride salt

HRID 1371478Notes

Reaction equation

HRID 1371478 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[OH:13][C:14]1[CH:23]=[C:22]2[C:17]([C:18]([NH:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27]4[O:31][CH2:32][O:33][C:26]=34)=[N:19][CH:20]=[N:21]2)=[CH:16][C:15]=1[O:34][CH3:35].[CH3:36][S:37]([CH2:40][CH2:41][CH2:42]O)(=[O:39])=[O:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)[Cl:64]>>[ClH:64].[CH3:35][O:34][C:15]1[CH:16]=[C:17]2[C:22](=[CH:23][C:14]=1[O:13][CH2:42][CH2:41][CH2:40][S:37]([CH3:36])(=[O:39])=[O:38])[N:21]=[CH:20][N:19]=[C:18]2[NH:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]2[O:31][CH2:32][O:33][C:26]=12

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 11776Triphenylphosphine2×HCID 2004243-(Methylsulfonyl)-1-propanol2×HCID 220568ethyl N-ethoxycarbonyliminocarbamate2×HCID 1355941137-Hydroxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinazoline

Product 1

HCID 219359896-Methoxy-4-(2,3-methylenedioxyanilino)-7-(3-methylsulphonylpropoxy)quinazoline monohydrochloride salt

Procedure

Diethyl azodicarboxylate (0.101 ml) was added dropwise to a stirred mixture of 7-hydroxy-6-methoxy-4-(2,3-methylenedioxyanilino)quinazoline (0.1 g), 3-methylsulphonylpropan-1-ol (0.057 g), triphenylphosphine (0.168 g) and methylene chloride (5 ml) and the reaction mixture was stirred at ambient temperature. After a few minutes further portions of triphenylphosphine (0.084 g) and 3-methylsulphonylpropan-1-ol (0.022 g) were added followed by the dropwise addition of diethyl azodicarboxylate (0.050 ml). After another few minutes third portions of the same amounts of these reagents were added. The reaction mixture was evaporated and the residue was purified by column chromatography on silica using a 10:6:1 mixture of methylene chloride, ethyl acetate and methanol as eluent. The material so obtained was triturated under a 6M solution of hydrogen chloride in diethyl ether. There was thus obtained the title compound (0.108 g) as a white solid; NMR Spectrum: (DMSOd6 and CF3CO2D) 2.3 (m, 2H), 3.05 (s, 3H), 3.35 (m, 2H), 4.0 (s, 3H), 4.35 (t, 2H), 6.1 (s, 2H), 7.0 (m, 3H), 7.3 (s, 1H), 8.1 (s, 1H), 8.15 (s, 1H); Mass Spectrum: M+H+ 432.

Workup

  1. additionAfter another few minutes third portions of the same amounts of these reagents were added
  2. customThe reaction mixture was evaporated
  3. customthe residue was purified by column chromatography on silica using
  4. additiona 10:6:1 mixture of methylene chloride, ethyl acetate and methanol as eluent
  5. customThe material so obtained
  6. customwas triturated under a 6M solution of hydrogen chloride in diethyl ether

Sources & evidence

ORD record
ord-14a6c9fc2ba2423ebcce9d1c940052bb
Source dataset
uspto-grants-2007_01
Patent number
US07157467B2

Reaction notes

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