Tetrahydrofuran → HCID 57382974, compound

HRID 2168248Notes

Reaction equation

HRID 2168248 reaction equation
[Br:1][C:2]1[C:10]2[C:9]([N:11]3[CH2:16][CH2:15][CH:14]([N:17]([CH3:26])[C:18]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=[O:19])[CH2:13][CH2:12]3)=[N:8][CH:7]=[N:6][C:5]=2[N:4](S(C2C=CC=CC=2)(=O)=O)[CH:3]=1.O1CCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>CO>[Br:1][C:2]1[C:10]2[C:9]([N:11]3[CH2:12][CH2:13][CH:14]([N:17]([CH3:26])[C:18]([C:20]4[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=4)=[O:19])[CH2:15][CH2:16]3)=[N:8][CH:7]=[N:6][C:5]=2[NH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 67988170HCID 67988170, compound

Product 1

HCID 57382974HCID 57382974, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-{1-[5-bromo-7-(phenylsulfonyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-4-piperidinyl}-N-methyl-4-pyridinecarboxamide D26 (41 mg) was dissolved with Tetrahydrofuran (THF) (1 mL) and Methanol (0.500 mL). Cesium carbonate (72.2 mg, 0.221 mmol) was added. The mixture was stirred at room temperature for 30 min. The mixture was partitioned between ethyl acetate (15 mL) and water (5 mL). The aqueous layer was extracted with ethyl acetate (15 mL). The combined organic phase was filtered by a phase separator and the solvent was removed in vacuo. The crude material was purified by MDAP. Evaporated the solvent and put in the vacuum oven to give the product E39 in 0.0168 g as a white powder. LCMS [M+H]+414.94/[email protected] min (5 min run)

Workup

  1. customThe mixture was partitioned between ethyl acetate (15 mL) and water (5 mL)
  2. extractionThe aqueous layer was extracted with ethyl acetate (15 mL)
  3. filtrationThe combined organic phase was filtered by a phase separator
  4. customthe solvent was removed in vacuo
  5. customThe crude material was purified by MDAP
  6. customEvaporated the solvent
  7. customto give the product
  8. customLCMS [M+H]+414.94/[email protected] min (5 min run)

Sources & evidence

ORD record
ord-74fc0e210d014cc09a97066a4eaea0f9
Source dataset
uspto-grants-2015_06
Patent number
US09045485B2

Reaction notes

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