Diisopropylethylamine → HCID 66584167, compound

HRID 467607Notes

Reaction equation

HRID 467607 reaction equation
Cl.[F:2][CH:3]1[CH2:8][CH2:7][CH2:6][NH:5][CH2:4]1.[Cl:9][C:10]1[CH:11]=[C:12]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:35][CH3:36])=[C:25]([NH:28][C:29](=[O:34])[CH:30]=[CH:31][CH2:32]Cl)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:13]=[CH:14][C:15]=1[F:16].CCN(C(C)C)C(C)C>C1COCC1.C(OCC)(=O)C>[Cl:9][C:10]1[CH:11]=[C:12]([NH:17][C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:35][CH3:36])=[C:25]([NH:28][C:29](=[O:34])[CH:30]=[CH:31][CH2:32][N:5]4[CH2:6][CH2:7][CH2:8][CH:3]([F:2])[CH2:4]4)[CH:26]=3)[N:21]=[CH:20][N:19]=2)[CH:13]=[CH:14][C:15]=1[F:16]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 27591563-FLUOROPIPERIDINE HYDROCHLORIDEHCID 66584297HCID 66584297, compound

Product 1

HCID 66584167HCID 66584167, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

99 mg 3-Fluoro-piperidine hydrochloride, 300 mg 4-Chloro-but-2-enoic acid [4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazolin-6-yl]-amide and 0.37 ml of DIEA were dissolved in 5 ml THF stirred at 70° C. overnight. The mixture was then diluted with ethyl acetate, washed with water and brine and dried over Na2SO4. The resulting solids were flash chromatographed with 0-4% methanol in chloroform to give 275 mg of 4-(3-Fluoro-piperidin-1-yl)-but-2-enoic acid [4-(3-chloro-4-fluoro-phenylamino)-7-methoxy-quinazolin-6-yl]-amide.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. customchromatographed with 0-4% methanol in chloroform

Sources & evidence

ORD record
ord-4cc110eba0d14cffb3c63354642c89d9
Source dataset
uspto-grants-2014_01
Patent number
US08623883B2

Reaction notes

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