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5-Chloro-1,3-benzodioxol-4-amine → N-(5-chloro-1,3-benzodioxol-4-yl)-5-morpholin-4-yl-7-(2-pyrrolidin-1-ylethoxy)quinazolin-4-amine

HRID 641783
Notes
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Reaction equation

HRID 641783 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:18][CH2:19][CH2:20][N:21]3[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:9][C:10]=2[N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:5]=[CH:4][N:3]=1.[Cl:26][C:27]1[C:32]([NH2:33])=[C:31]2[O:34][CH2:35][O:36][C:30]2=[CH:29][CH:28]=1>C(O)(C)C>[Cl:26][C:27]1[C:32]([NH:33][C:2]2[C:11]3[C:6](=[CH:7][C:8]([O:18][CH2:19][CH2:20][N:21]4[CH2:25][CH2:24][CH2:23][CH2:22]4)=[CH:9][C:10]=3[N:12]3[CH2:17][CH2:16][O:15][CH2:14][CH2:13]3)[N:5]=[CH:4][N:3]=2)=[C:31]2[O:34][CH2:35][O:36][C:30]2=[CH:29][CH:28]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 113672535-Chloro-1,3-benzodioxol-4-amineHCID 221407094-Chloro-5-morpholino-7-(2-pyrrolidin-1-ylethoxy)quinazoline

Product 1

HCID 11974116N-(5-chloro-1,3-benzodioxol-4-yl)-5-morpholin-4-yl-7-(2-pyrrolidin-1-ylethoxy)quinazolin-4-amineYield 9.4%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-chloro-5-morpholino-7-(2-pyrrolidin-1-ylethoxy)quinazoline (0.27 g), 6-chloro-2,3-methylenedioxyaniline (0.14 g) and isopropanol (4 ml) was stirred and heated to 80° C. for 1 hour. The mixture was evaporated and the residue was dissolved in a 49:1 mixture of methylene chloride and a saturated methanolic ammonia solution. The mixture was filtered and the filtrate was poured onto a column of silica and eluted with a 97:3 mixture of methylene chloride and a saturated methanolic ammonia solution. The material so obtained was triturated under diethyl ether. The resultant solid was isolated, washed with diethyl ether and dried under vacuum. There was thus obtained the title compound (0.035 g); NMR Spectrum: (CDCl3) 1.85 (br s, 4H), 2.65 (br s, 4H), 3.0 (m, 2H), 3.08 (m, 2H), 3.18 (d, 2H), 3.82 (m, 2H), 4.05 (m, 2H), 4.25 (m, 2H), 6.05 (s, 2H), 6.75 (d, 1H), 6.95-7.1 (m, 3H), 8.52 (s, 1H); Mass Spectrum: M+H+ 498 and 500.

Workup

  1. customThe mixture was evaporated
  2. dissolutionthe residue was dissolved in a 49:1 mixture of methylene chloride
  3. filtrationThe mixture was filtered
  4. additionthe filtrate was poured onto a column of silica
  5. washeluted with a 97:3 mixture of methylene chloride
  6. customThe material so obtained
  7. customwas triturated under diethyl ether
  8. customThe resultant solid was isolated
  9. washwashed with diethyl ether
  10. customdried under vacuum

Sources & evidence

ORD record
ord-f20da184c2cb463fb3d623f89b56b373
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07696214B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes