Diisopropylethylamine → HCID 49773731, compound

HRID 1025531Notes

Reaction equation

HRID 1025531 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:19][CH2:20][C:21]([F:24])([F:23])[F:22])[C:5]2[N:11]=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[NH2:25][CH2:26][C:27]1[CH:37]=[CH:36][C:30]([C:31]([N:33]([CH3:35])[CH3:34])=[O:32])=[CH:29][CH:28]=1.C(N(C(C)C)CC)(C)C.O.C(#N)C>CN1C(=O)CCC1>[F:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[CH:8][C:6]3[N:7]=[C:2]([NH:25][CH2:26][C:27]4[CH:28]=[CH:29][C:30]([C:31]([N:33]([CH3:34])[CH3:35])=[O:32])=[CH:36][CH:37]=4)[N:3]=[C:4]([NH:19][CH2:20][C:21]([F:24])([F:23])[F:22])[C:5]=3[N:11]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 162278764-(aminomethyl)-N,N-dimethylbenzamideHCID 18373917Acetonitrile--water (1/1)HCID 58275412HCID 58275412, compound

Product 1

HCID 49773731HCID 49773731, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

[2-Chloro-6-(4-fluoro-phenyl)-pyrido[3,2-d]pyrimidin-4-yl]-(2,2,2-trifluoroethyl)-amine (100 mg, 0.28 mmol), 4-aminomethyl-N,N-dimethyl-benzamide (100 mg, 0.56 mmol) and diisopropylethylamine (0.097 mL, 0.56 mmol) were suspended in NMP (1.5 mL), sealed and heated by microwave to 140 deg C. for 1 h. After cooling the reaction mixture was added dropwise to a stirring mixture of water/acetonitrile (8 mL, 3:1) to afford a yellow precipitate. The solid was filtered, washed with water, dissolved in hot dioxane and concentrated onto silica gel. Purification by flash chromatography (0-10%, EtOH (containing 11% saturated aqueous ammonium hydroxide) in dichloromethane) to afford 21 mg (15%) of the desired product as a white solid. MS (m/z) 499.3 [M+H]+.

Workup

  1. customsealed
  2. temperatureheated by microwave to 140 deg C
  3. temperatureAfter cooling the reaction mixture
  4. customto afford a yellow precipitate
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. dissolutiondissolved in hot dioxane
  8. concentrationconcentrated onto silica gel
  9. customPurification by flash chromatography (0-10%, EtOH (containing 11% saturated aqueous ammonium hydroxide) in dichloromethane)

Sources & evidence

ORD record
ord-0e88193e69194a8eb628eaf01b24adc7
Source dataset
uspto-grants-2014_05
Patent number
US08729089B2

Reaction notes

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