Sodium Hydroxide → HCID 178486858, compound

HRID 241241Notes

Reaction equation

HRID 241241 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([CH:6]([CH:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18]2[CH:19]=[C:20]3[C:25](=[CH:26][C:27]=2[O:28][CH3:29])[N:24]=[CH:23][N:22]=[C:21]3[NH:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([Cl:37])[C:32]=2[F:38])[CH2:13][CH2:12]1)[C:7]([O:9]C)=O)[CH3:5].[OH-].[Na+]>CO>[Cl:37][C:33]1[C:32]([F:38])=[C:31]([NH:30][C:21]2[C:20]3[C:25](=[CH:26][C:27]([O:28][CH3:29])=[C:18]([O:17][C@H:14]4[CH2:13][CH2:12][C@H:11]([C@@H:6]5[N:4]([CH3:5])[CH2:3][CH2:2][NH:1][C:7]5=[O:9])[CH2:16][CH2:15]4)[CH:19]=3)[N:24]=[CH:23][N:22]=2)[CH:36]=[CH:35][CH:34]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 76737747HCID 76737747, compound

Product 1

HCID 178486858HCID 178486858, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 700 mg methyl [(2-amino-ethyl)-methyl-amino]-{4-[4-(3-chloro-2-fluoro-phenylamino)-7-methoxy-quinazolin-6-yloxy]-cyclohexyl}-acetate, 7 ml of methanol and 0.65 ml 4N sodium hydroxide solution is stirred for three hours at ambient temperature. Then the reaction mixture is evaporated down and extracted with ethyl acetate. The organic phase is dried on magnesium sulphate and evaporated down. The flask residue is purified by chromatography through a silica gel column with methylene chloride/methanol/conc. ammonia (98/2/0.1 auf 8/2/0.1) as eluant. The crude product is stirred with diisopropylether, suction filtered and dried.

Workup

  1. customThen the reaction mixture is evaporated down
  2. extractionextracted with ethyl acetate
  3. customThe organic phase is dried on magnesium sulphate
  4. customevaporated down
  5. customThe flask residue is purified by chromatography through a silica gel column with methylene chloride/methanol/conc
  6. stirringThe crude product is stirred with diisopropylether, suction
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-2606aa286fbf4c49b9bbea94a1e643fd
Source dataset
uspto-grants-2014_02
Patent number
US08648191B2

Reaction notes

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