Triethylamine → HCID 71767957, compound

HRID 530218Notes

Reaction equation

HRID 530218 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:16][CH:15]=1)=[CH:10][C:9]([NH:27][C:28](=[O:35])/[CH:29]=[CH:30]/CN(C)C)=[CH:8][CH:7]=2)#[N:2].C(N(CC)CC)C.C(Cl)(=O)C=C.NC1C=C2C(=CC=1)N=CC(C#N)=C2NC1C=CC(OC2C=CC=CC=2)=CC=1>C1COCC1.O>[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:12]=1[NH:13][C:14]1[CH:15]=[CH:16][C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:18][CH:19]=1)=[CH:10][C:9]([NH:27][C:28](=[O:35])[CH:29]=[CH2:30])=[CH:8][CH:7]=2)#[N:2]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 71767519HCID 71767519, compoundHCID 89852603HCID 89852603, compound

Product 1

HCID 71767957HCID 71767957, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Example 3 was prepared as an off-white solid using a procedure similar to that described for the synthesis of compound 21 (Example 2). Triethylamine (1.03 g, 10.2 mmol, 1.2 eq) and acryloyl chloride (926 mg, 10.2 mmol, 1.2 eq) were added to an ice cold solution of 6-amino-4-((4-phenoxyphenyl)amino)quinoline-3-carbonitrile (3.0 g, 8.5 mmol, 1.0 eq) in THF (50 mL) under nitrogen. The reaction was stirred at rt for 2 hours. The water was added. The water layer was extracted with EA, dried over anhydrous sodium sulfate. The crude product was purified by column chromatography on silica gel to give N-(3-cyano-4-((4-phenoxyphenyl)amino)quinolin-6-yl)acrylamide as an off-white solid 1.2 g.

Workup

  1. customExample 3 was prepared as an off-white solid
  2. extractionThe water layer was extracted with EA
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-198e82347c9e4e4796127c02cb89a202
Source dataset
uspto-grants-2016_05
Patent number
US09353062B2

Reaction notes

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