Acetic Acid → HCID 58382031, compound

HRID 1628080Notes

Reaction equation

HRID 1628080 reaction equation
[CH3:1][Mg]Cl.[CH3:4][N:5]1[C:13]2[C:8](=[CH:9][C:10](C(OC)=O)=[CH:11][CH:12]=2)[C:7]([C:18]2[N:30]([S:31]([C:34]3[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=3)(=[O:33])=[O:32])[C:21]3=[N:22][CH:23]=[C:24]4[CH:28]=[N:27][N:26]([CH3:29])[C:25]4=[C:20]3[CH:19]=2)=[CH:6]1.[CH3:41][C:42]([OH:44])=O>C1COCC1.O>[CH3:4][N:5]1[C:13]2[C:8](=[CH:9][C:10]([C:42]([OH:44])([CH3:41])[CH3:1])=[CH:11][CH:12]=2)[C:7]([C:18]2[N:30]([S:31]([C:34]3[CH:40]=[CH:39][C:37]([CH3:38])=[CH:36][CH:35]=3)(=[O:32])=[O:33])[C:21]3=[N:22][CH:23]=[C:24]4[CH:28]=[N:27][N:26]([CH3:29])[C:25]4=[C:20]3[CH:19]=2)=[CH:6]1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 58382155HCID 58382155, compoundHCID 178418332HCID 178418332, compound

Product 1

HCID 58382031HCID 58382031, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of MeMgCl (3 M in THF, 0.65 mL, 1.95 mmol) in THF (4 mL) was cooled to about −40° C. then methyl 1-methyl-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indole-5-carboxylate (0.125 g, 0.243 mmol, prepared using D from Preparation #1 and Preparation #18 in THF (3 mL) was added. The mixture was warmed to rt and stirred for about 1 h. The mixture was treated with AcOH (˜0.75 mL) then the mixture was diluted with water (30 mL). The mixture was extracted with EtOAc (2×25 mL). The combined organics were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo to give 2-(1-methyl-3-(1-methyl-6-tosyl-1,6-dihydropyrazolo[3,4-d]pyrrolo[2,3-b]pyridin-7-yl)-1H-indol-5-yl)propan-2-ol (0.115 g, 92%): LC/MS (Table 2, Method a) Rt=2.26 min; MS m/z 514 (M+H)+.

Workup

  1. additionwas added
  2. extractionThe mixture was extracted with EtOAc (2×25 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-91e46f7d90d64bd1b0509e10d4a8cc2b
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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