Lithium Hydroxide → N-(3-(3-(1-(2-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide

HRID 531466Notes

Reaction equation

HRID 531466 reaction equation
[F:1][C:2]1[CH:43]=[CH:42][CH:41]=[CH:40][C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([NH:25][S:26]([CH3:29])(=[O:28])=[O:27])[CH:22]=[CH:23][CH:24]=4)[CH:17]=3)[N:12](S(C3C=CC(C)=CC=3)(=O)=O)[CH:11]=2)[CH:7]=[N:6]1.[OH-].[Li+]>C1COCC1.O.CO.CCCCCC.C(OCC)(=O)C>[F:1][C:2]1[CH:43]=[CH:42][CH:41]=[CH:40][C:3]=1[CH2:4][N:5]1[CH:9]=[C:8]([C:10]2[C:18]3[C:13](=[N:14][CH:15]=[C:16]([C:19]4[CH:20]=[C:21]([NH:25][S:26]([CH3:29])(=[O:27])=[O:28])[CH:22]=[CH:23][CH:24]=4)[CH:17]=3)[NH:12][CH:11]=2)[CH:7]=[N:6]1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 118523933N-(3-(3-(1-(2-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide

Product 1

HCID 72944747N-(3-(3-(1-(2-fluorobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamideYield 14.99%

Reagents, catalysts & solvents 3

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

N-(3-(3-(1-(2-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl) methanesulfonamide (200 mg) dissolved in 12.5 ml of THF-water-methanol (1:1:0.5) mixture and added lithium hydroxide (40.8 mg, 0.97 mmol) at 0° C. and stirred at room temperature for 15 h. The reaction was monitored by TLC (100% ethyl acetate in hexane) until TLC indicated that reaction was complete. The reaction mixture was diluted with ethyl acetate (25 ml) and washed with water (2×25 ml). The organic layer was dried over Na2SO4, and concentrated under reduced pressure to afford crude product. Purification by preparative TLC (5% methanol in DCM) afforded 17 mg (14.99% yield) of tilted compound. 1H NMR (DMSO-d6, 300 MHz): δ 9.83 (s, 1H), 8.479-8.472 (d, 1H), 8.38 (s, 1H), 8.33-8.32 (d, 1H), 7.95-7.78 (m, 2H), 7.53-7.43 (m, 4H), 7.27-7.18 (m, 3H), 5.44 (s, 2H), 3.05 (s, 1H). MS: m/z=462.1 (M+1), HPLC: 95.83% in method A.

Workup

  1. customindicated that reaction
  2. washwashed with water (2×25 ml)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated under reduced pressure
  5. customto afford crude product
  6. customPurification by preparative TLC (5% methanol in DCM)

Sources & evidence

ORD record
ord-fefaee633c984ff39051341d83e5c4c0
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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