HCID 59238643, compound → HCID 59238778, compound

HRID 1924466Notes

Reaction equation

HRID 1924466 reaction equation
[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[C:2]2[C:8]1[CH:9]=[C:10]2[C:16]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)=[CH:15][N:14](S(C3C=CC=CC=3)(=O)=O)[C:11]2=[N:12][CH:13]=1>CCO.[OH-].[Na+]>[CH:1]12[CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]=[C:2]2[C:8]1[CH:9]=[C:10]2[C:16]([C:17]3[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=3)=[CH:15][NH:14][C:11]2=[N:12][CH:13]=1

Participants

4

Reactant 1

HCID 59238643HCID 59238643, compound

Product 1

HCID 59238778HCID 59238778, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

5-(bicyclo[2.2.1]hept-2-en-2-yl)-3-(1-methyl-1H-pyrazol-4-yl)-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine 2 (63 mg, 0.146 mmol) in EtOH (1.50 mL) and 10% aqueous NaOH (0.75 mL), was deprotected as described in the general procedure A for the deprotection of 7-azaindoles by refluxing for 20 min. The reaction was quenched by addition of a saturated solution of NaHCO3 (15 mL) and the mixture was stirred for 20 minutes. It was extracted with EtOAc (3×15 mL). The combined organic extracts were dried over MgSO4 and concentrated. The crude product purified by PTLC using EtOAc as the eluent to give (I-136) (24.8 mg, 58%). 1H NMR (400 MHz, CDCl3) δ 1.16-1.25 (m, 2H), 1.32 (d, J=8.2 Hz, 1H), 1.59-1.63 (m, 1H), 1.80-1.89 (m, 2H), 3.04-3.08 (m, 1H), 3.42-3.45 (br s, 1H), 4.01 (s, 3H), 6.35 (d, J=3.1 Hz, 1H), 7.39 (d, J=2.3 Hz, 1H), 7.64 (s, 1H), 7.78 (d, J=0.5 Hz, 1H), 8.04 (d, J=2.0 Hz, 1H), 8.49 (d, J=2.0 Hz, 1H), 10.09 (br s, NH, 1H).

Workup

  1. temperatureby refluxing for 20 min
  2. customThe reaction was quenched by addition of a saturated solution of NaHCO3 (15 mL)
  3. extractionIt was extracted with EtOAc (3×15 mL)
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. concentrationconcentrated
  6. customThe crude product purified by PTLC
  7. customto give (I-136) (24.8 mg, 58%)

Sources & evidence

ORD record
ord-c17ec8ce4879495cac5c23efe4917dcf
Source dataset
uspto-grants-2012_05
Patent number
US08178552B2

Reaction notes

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