Sulfuric Acid → 4-[4-(3-Chloro-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-yloxy]-cyclohexanone

HRID 1672121Notes

Reaction equation

HRID 1672121 reaction equation
S(=O)(=O)(O)O.[Cl:6][C:7]1[C:8]([F:37])=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:35][CH3:36])=[C:21]([O:24][CH:25]4[CH2:34][CH2:33][C:28]5(OCC[O:29]5)[CH2:27][CH2:26]4)[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1.[OH-].[Na+]>O1CCCC1>[Cl:6][C:7]1[C:8]([F:37])=[C:9]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([O:35][CH3:36])=[C:21]([O:24][CH:25]4[CH2:34][CH2:33][C:28](=[O:29])[CH2:27][CH2:26]4)[CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 591581734-[(3-Chloro-2-fluoro-phenyl)amino]-6-(1,4-dioxa-spiro[4.5]decan-8-yl-oxy)-7-methoxy-quinazoline

Product 1

HCID 581572644-[4-(3-Chloro-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-yloxy]-cyclohexanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

25 ml 4M sulphuric acid are added to 9.0 g 4-[(3-chloro-2-fluoro-phenyl)amino]-6-(1,4-dioxa-spiro[4.5]decan-8-yl-oxy)-7-methoxy-quinazoline in 110 ml of tetrahydrofuran and the mixture is stirred for 18 hours at ambient temperature. The mixture is made alkaline with 4M sodium hydroxide solution and extracted several times with ethyl acetate. The combined organic phases are dried, evaporated down and stirred with diethyl ether. The solid is suction filtered and dried.

Workup

  1. extractionextracted several times with ethyl acetate
  2. customThe combined organic phases are dried
  3. customevaporated down
  4. stirringstirred with diethyl ether
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-cde960a1631246b986a613cd8c308350
Source dataset
uspto-grants-2011_08
Patent number
US07998949B2

Reaction notes

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