MeOH tetrahydrofuran → HCID 178432026, compound

HRID 1257679Notes

Reaction equation

HRID 1257679 reaction equation
C1(S([N:10]2[CH:21]=[CH:20][C:19]3[C:11]2=[N:12][CH:13]=[C:14]2[C:18]=3[N:17]([C:22]3([CH3:37])[CH2:27][CH2:26][N:25]([S:28]([C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)(=[O:30])=[O:29])[CH2:24][CH2:23]3)[N:16]=[N:15]2)(=O)=O)C=CC=CC=1.C1COCC1.CO>>[CH3:37][C:22]1([N:17]2[C:18]3[C:14](=[CH:13][N:12]=[C:11]4[C:19]=3[CH:20]=[CH:21][NH:10]4)[N:15]=[N:16]2)[CH2:27][CH2:26][N:25]([S:28]([C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)(=[O:30])=[O:29])[CH2:24][CH2:23]1

Participants

3

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 67345279HCID 67345279, compound

Product 1

HCID 178432026HCID 178432026, compoundYield 27%

Procedure

A mixture of 6-benzenesulfonyl-1-[4-methyl-1-(pyridine-3-sulfonyl)-piperidin-4-yl]-1,6-dihydro-1,2,3,5,6-pentaaza-as-indacene (74.0 mg, 0.14 mmol) in THF/methanol containing aqueous sodium hydroxide (0.53 mmol) was stirred for 64 hr. The solvent was evaporated under vacuum to a small volume, the residue dissolved in DCM, washed with saturated sodium bicarbonate solution and brine, dried over sodium sulfate and concentrated under vacuum and the resulting residue purified by column chromatography on silica gel (gradient: 0 to 5% [2M NH3 in methanol] in DCM) to afford 15.0 mg (27%) of 1-[4-methyl-1-(pyridine-3-sulfonyl)-piperidin-4-yl]-1,6-dihydro-1,2,3,5,6-pentaaza-as-indacene. LCMS (Method A, ESI): RT=3.42 min, m+H=398.2; 1H NMR (400 MHz, DMSO): δ 12.45 (s, 1H), 8.99 (s, 1H), 8.86 (m, 2H), 8.13 (ddd, 1H), 7.65 (m, 2H), 6.91 (dd, 1H), 3.49 (m, 2H), 2.90 (m, 2H), 2.75 (m, 2H), 2.31 (m, 2H), 1.75 (s, 3H).

Workup

  1. customThe solvent was evaporated under vacuum to a small volume
  2. dissolutionthe residue dissolved in DCM
  3. washwashed with saturated sodium bicarbonate solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customthe resulting residue purified by column chromatography on silica gel (gradient: 0 to 5% [2M NH3 in methanol] in DCM)

Sources & evidence

ORD record
ord-160833e7d5754f6b892a1989ab13cd70
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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