MeOH tetrahydrofuran → HCID 178451969, compound

HRID 1257674Notes

Reaction equation

HRID 1257674 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([N:15]2[C:26]3[C:18](=[CH:19][N:20]=[C:21]4[C:25]=3[CH:24]=[CH:23][N:22]4S(C3C=CC=CC=3)(=O)=O)[NH:17][N:16]2C)([CH3:14])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1COCC1.CO>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH3:14])([N:15]2[C:26]3[C:18](=[CH:19][N:20]=[C:21]4[C:25]=3[CH:24]=[CH:23][NH:22]4)[N:17]=[N:16]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 2

HCID 21899815MeOH tetrahydrofuranHCID 67345148HCID 67345148, compound

Product 1

HCID 178451969HCID 178451969, compoundYield 90%

Procedure

A mixture of 4-(6-benzenesulfonyl-2-methyl-6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-4-methyl-piperidine-1-carboxylic acid tert-butyl ester (0.37 g, 0.75 mmol) in THF/methanol containing aqueous sodium hydroxide (3.75 mmol) was stirred for 16 hours. 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 to afford 240 mg (90%) of 4-methyl-4-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-piperidine-1-carboxylic acid tert butyl ester. LCMS (Method I, ESI): RT=3.20 min, m+H=357.3; 1H NMR (400 MHz, DMSO) δ: 12.46 (s, 1H), 9.06 (s, 1H), 7.63 (t, 1H), 6.86 (m, 1H), 3.62 (m, 2H), 3.33 (m, 2H), 2.71 (m, 2H), 2.12 (m, 2H), 1.85 (s, 3H), 1.43 (s, 9H).

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

Sources & evidence

ORD record
ord-7add012584d741dc95b3240dfa31a46f
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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