Ethyl Acetate → HCID 57019768, compound

HRID 488423Notes

Reaction equation

HRID 488423 reaction equation
O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:50][CH2:51][CH:52]4[CH2:54][CH2:53]4)=[C:29]([NH:32][C:33](=[O:49])[CH:34]=[CH:35][CH2:36][N:37]([CH2:43][C:44]([O:46]CC)=[O:45])[CH2:38][C:39](O)([CH3:41])[CH3:40])[CH:30]=3)[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[F:20].C(OCC)(=O)C>C(#N)C>[Cl:13][C:14]1[CH:15]=[C:16]([NH:21][C:22]2[C:31]3[C:26](=[CH:27][C:28]([O:50][CH2:51][CH:52]4[CH2:54][CH2:53]4)=[C:29]([NH:32][C:33](=[O:49])[CH:34]=[CH:35][CH2:36][N:37]4[CH2:43][C:44](=[O:46])[O:45][C:39]([CH3:41])([CH3:40])[CH2:38]4)[CH:30]=3)[N:25]=[CH:24][N:23]=2)[CH:17]=[CH:18][C:19]=1[F:20]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 54492519HCID 54492519, compound

Product 1

HCID 57019768HCID 57019768, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

15 mg of p-toluenesulphonic acid monohydrate are added to 150 mg of 4-[(3-chloro-4-fluorophenyl)amino]-6-[(4-{N-[(ethoxycarbonyl)methyl]-N-(2-hydroxy-2-methyl-propyl)amino}-1-oxo-2-buten-1-yl)amino]-7-cyclopropylmethoxy-quinazoline in 2.5 ml of acetonitrile. The solution formed is stirred first for three hours at ambient temperature, then refluxed for a further two hours until the reaction is complete. For working up, the reaction mixture is combined with 30 ml of ethyl acetate. The organic phase is separated off, washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution, dried over magnesium sulphate and concentrated by evaporation. The oily yellow residue is stirred with diethylether, whereupon a light yellow solid crystallises out, which is filtered off and dried. Yield: 85 mg (61% of theory), Melting point: 140-142° C. Mass spectrum (ESI+): m/z=554, 556 [M+H]+

Workup

  1. customThe solution formed
  2. temperaturerefluxed for a further two hours until the reaction
  3. customThe organic phase is separated off
  4. washwashed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated by evaporation
  7. stirringThe oily yellow residue is stirred with diethylether, whereupon a light yellow solid
  8. customcrystallises out, which
  9. filtrationis filtered off
  10. customdried

Sources & evidence

ORD record
ord-1cb55e4e5325466da58f8693f5749d4b
Source dataset
uspto-grants-2005_12
Patent number
US06972288B1

Reaction notes

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