Tetrahydrofuran → HCID 57477564, compound

HRID 1524658Notes

Reaction equation

HRID 1524658 reaction equation
[CH3:1][C:2]1[C:6]([C:7](O)=[O:8])=[CH:5][N:4]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:17]=[CH:18][C:11]=23)[N:3]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.C1COCC1.[NH:44]1[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]1>>[CH3:1][C:2]1[C:6]([C:7]([N:44]2[CH2:49][CH2:48][CH2:47][CH2:46][CH2:45]2)=[O:8])=[CH:5][N:4]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]3[N:16]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:25])[CH3:26])[CH:17]=[CH:18][C:11]=23)[N:3]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 8082Piperidine2×HCID 682631,1'-CarbonyldiimidazoleHCID 57477563HCID 57477563, compound

Product 1

HCID 57477564HCID 57477564, compoundYield 101.3%

Procedure

A solution of 3-methyl-1-(1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazole-4-carboxylic acid (0.040 g, 0.00011 mol) (1:1 of AcOH) and N,N-carbonyldiimidazole (0.035 g, 0.00021 mol) in THF (1 mL, 0.01 mol) was stirred for 1.2 h, after which time piperidine (32 μL, 0.00032 mol) was added. After another 2 h, another portion of piperidine (15 μL) was added and the resulting mixture was stirred overnight. The reaction mixture was then partitioned between ethyl acetate and water, and washed sequentially with sat. NaHCO3 and brine. The organic phase was dried and evaporated to give 49 mg of the crude product as an orange oil/glass. The crude product was chromatographed with 75-100% ethyl acetate/hexanes, sample in DCM. Collected 25 mg of the purified product as a colorless glass/oil (50% yield).

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate and water
  2. washwashed sequentially with sat. NaHCO3 and brine
  3. customThe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-b9aed11b58934418ac9a0ed0008a7d50
Source dataset
uspto-grants-2015_07
Patent number
US09079912B2

Reaction notes

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