Triethylamine → HCID 86690701, compound

HRID 711382Notes

Reaction equation

HRID 711382 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[C:13]([CH3:21])[N:14]([CH:15]4[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]4)[C:5]=3[C:4]=2[N:3]=1.CCN(CC)CC.[CH:29]1([C:32](Cl)=[O:33])[CH2:31][CH2:30]1>C1COCC1>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]=[C:13]([CH3:21])[N:14]([CH:15]4[CH2:20][CH2:19][N:18]([C:32]([CH:29]5[CH2:31][CH2:30]5)=[O:33])[CH2:17][CH2:16]4)[C:5]=3[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77637Cyclopropanecarbonyl chlorideHCID 86690702HCID 86690702, compound

Product 1

HCID 86690701HCID 86690701, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-chloro-2-methyl-1-(piperidin-4-yl)-1H-imidazo[4,5-c][1,5]naphthyridine (110 mg, 0.364 mmol) and Et3N (101 μL, 0.728 mmol) in THF (15 mL) was added cyclopropanecarbonyl chloride (36 μL, 0.401 mmol) while cooling with an ice-water bath. The reaction mixture was stirred at r.t. for 3 h, and was then concentrated under vacuum. The residue was dissolved in a mixture of CH2Cl2 (10 mL) and H2O (10 mL). The resulting solution was then extracted with EA (2×10 mL). The combined organic layers were concentrated to give crude (4-(8-chloro-2-methyl-1H-imidazo[4,5-c][1,5]naphthyridin-1-yl) piperidin-1-yl)(cyclopropyl)methanone as a yellow solid (105 mg, yield 80%) which was used in the next step without further purification. MS (m/z): 370 (M+H)+.

Workup

  1. temperaturewhile cooling with an ice-water bath
  2. concentrationwas then concentrated under vacuum
  3. dissolutionThe residue was dissolved in a mixture of CH2Cl2 (10 mL) and H2O (10 mL)
  4. extractionThe resulting solution was then extracted with EA (2×10 mL)
  5. concentrationThe combined organic layers were concentrated

Sources & evidence

ORD record
ord-63000fd7100e4af49292b21f30220b91
Source dataset
uspto-grants-2015_11
Patent number
US09181264B2

Reaction notes

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