Triethylamine → HCID 53882130, compound

HRID 488425Notes

Reaction equation

HRID 488425 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:32][CH2:33][CH:34]4[CH2:36][CH2:35]4)=[C:17]([NH:20][C:21](=[O:31])[CH:22]=[CH:23][CH2:24][N:25]4[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].C(N(CC)CC)C.Br[CH2:45][C:46]([O:48][CH2:49][C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:47]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:32][CH2:33][CH:34]4[CH2:35][CH2:36]4)=[C:17]([NH:20][C:21](=[O:31])[CH:22]=[CH:23][CH2:24][N:25]4[CH2:30][CH2:29][N:28]([CH2:45][C:46]([O:48][CH2:49][C:50]5[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=5)=[O:47])[CH2:27][CH2:26]4)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62576Benzyl bromoacetateHCID 53675098HCID 53675098, compound

Product 1

HCID 53882130HCID 53882130, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

500 mg of 4-[(3-chloro-4-fluoro-phenyl)amino]-6-{[4-(piperazin-1-yl)-1-oxo-2-buten-1-yl]amino}-7-cyclopropylmethoxy-quinazoline are dissolved in 5 ml of acetonitrile, and 0.35 ml of triethylamine followed by 0.17 ml of benzyl bromo-acetate are added dropwise at room temperature. The reaction mixture is stirred for approximately 45 minutes at room temperature and then concentrated in vacuo. The solid residue is triturated with water and filtered off. The crude product is purified by column chromatography on silica gel with methylene chloride/methanol (20:1) followed by recrystallization from ethyl acetate. Yield: 380 mg (59% of theory), Melting point: 174° C. Mass spectrum (ESI−): m/z=657, 659 [M−H]−

Workup

  1. additionare added dropwise at room temperature
  2. concentrationconcentrated in vacuo
  3. customThe solid residue is triturated with water
  4. filtrationfiltered off
  5. customThe crude product is purified by column chromatography on silica gel with methylene chloride/methanol (20:1)
  6. customfollowed by recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-9efbbfd8aa61496ca5e6e09793823fbc
Source dataset
uspto-grants-2005_12
Patent number
US06972288B1

Reaction notes

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