Diisopropylethylamine → HCID 90388508, compound

HRID 2205238Notes

Reaction equation

HRID 2205238 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:19][C:18]4[C:17]([OH:20])=[CH:16][N:15]=[CH:14][C:13]=4[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1.[CH3:21]CN(C(C)C)C(C)C.[Si](C=[N+]=[N-])(C)(C)C>C(Cl)Cl.CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([C:11]3[S:19][C:18]4[C:17]([O:20][CH3:21])=[CH:16][N:15]=[CH:14][C:13]=4[CH:12]=3)=[CH:9][N:10]=2)[N:7]=1

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 167693TrimethylsilyldiazomethaneHCID 90388219HCID 90388219, compound

Product 1

HCID 90388508HCID 90388508, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(6-chloroimidazo[1,2-b]pyridazin-3-yl)thieno[3,2-c]pyridin-7-ol (38 mg, 0.126 mmol, 1.0 equiv) in DCM (3.0 mL) and MeOH (1.0 mL) was added DIPEA (0.188 mmol, 1.5 equiv) then TMSCHN2 (94 microliter, 0.188 mmol, 1.5 equiv). The reaction mixture was stirred at rt for 3 h, then quenched with water and extracted with ethyl acetate. Purification by column chromatography using 20% ethyl acetate in hexanes elution gave 20 mg of the yellow solid, 50%.

Workup

  1. customquenched with water
  2. extractionextracted with ethyl acetate
  3. customPurification by column chromatography
  4. wash20% ethyl acetate in hexanes elution

Sources & evidence

ORD record
ord-3fa7ff2b52f045f7aef7f4f86a4afc68
Source dataset
uspto-grants-2016_06
Patent number
US09370515B2

Reaction notes

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