Chloroacetyl chloride → HCID 56592663, compound

HRID 714587Notes

Reaction equation

HRID 714587 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:37][CH:38]4[CH2:42][CH2:41][O:40][CH2:39]4)=[C:24]([NH:27][C:28](=[O:36])[CH:29]=[C:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)[CH:25]=3)[N:20]=[CH:19][C:18]=2[C:43]#[N:44])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1.[CH2:45]1[CH2:49][O:48][CH2:47][CH2:46]1.ClCC(Cl)=[O:53].[NH2:55][CH2:56][CH2:57][O:58]C(O)C>C(#N)C.C(N(CC)CC)C>[Cl:1][C:2]1[CH:3]=[C:4]([NH:16][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:37][CH:38]4[CH2:42][CH2:41][O:40][CH2:39]4)=[C:24]([NH:27][C:28](=[O:36])[CH:29]=[C:30]4[CH2:35][CH2:34][N:33]([C:57](=[O:58])[CH2:56][NH:55][CH2:46][CH2:47][O:48][CH2:49][CH2:45][OH:53])[CH2:32][CH2:31]4)[CH:25]=3)[N:20]=[CH:19][C:18]=2[C:43]#[N:44])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 21989213HCID 21989213, compoundHCID 56591959HCID 56591959, compound

Product 1

HCID 56592663HCID 56592663, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent2×

Procedure

To a single-neck reaction flask (50 ml) were added N-(4-(3-chloro-4-(pyridin-2-yl-methoxy)phenylamino)-3-cyano-7-(tetrahydrofuran-3-yl-oxy)quinolin-6-yl)-2-(piperidin-4-ylidene)acetamide (20 mg, 0.041 mmol) and anhydrous THF (10 ml). The solution was cooled in an ice bath. Chloroacetyl chloride (4.5 mg) and anhydrous triethylamine (0.02 ml) were added into the solution. The resultant mixture was continuously stirred. After the reaction finished, the solvent was rotary-evaporated to dryness. The residue was dissolved in chloroform. The solution was washed with water three times and with saturated saline solution once. The resultant solution was dried over anhydrous magnesium sulfate, filtered and rotary-evaporated to dryness. The above resulting crude product was dissolved in acetonitrile (10 ml). To the solution were added aminoethoxyethanol (4 mg) and triethylamine (0.2 ml). The mixture was stirred at the room temperature. After the reaction finished, the solvent was rotary-evaporated to dryness. The resultant substance was purified with thin layer chromatography (developing solvent: chloroform methanol=9:1.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. customthe solvent was rotary-evaporated to dryness
  3. dissolutionThe residue was dissolved in chloroform
  4. washThe solution was washed with water three times and with saturated saline solution once
  5. dry with materialThe resultant solution was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customrotary-evaporated to dryness
  8. customThe above resulting crude product
  9. customthe solvent was rotary-evaporated to dryness
  10. customThe resultant substance was purified with thin layer chromatography (

Sources & evidence

ORD record
ord-98209f8bef2e472b8f2446c0c699ab2a
Source dataset
uspto-grants-2015_11
Patent number
US09187458B2

Reaction notes

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