HCID 67345148, compound → HCID 67343253, compound

HRID 1257677Notes

Reaction equation

HRID 1257677 reaction equation
C(OC([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]4[S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)(=[O:29])=[O:28])[NH:17][N:16]2C)([CH3:14])[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[C:30]1([S:27]([N:22]2[CH:23]=[CH:24][C:25]3[C:21]2=[N:20][CH:19]=[C:18]2[C:26]=3[N:15]([C:11]3([CH3:14])[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]3)[N:16]=[N:17]2)(=[O:29])=[O:28])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1

Participants

3

Reactant 1

HCID 67345148HCID 67345148, compound

Product 1

HCID 67343253HCID 67343253, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

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 (280 mg, 0.56 mmol)) in DCM/TFA was stirred for 1 hr. The solvent was evaporated under vacuum and the resulting residue purified by column chromatography (SCX-2, gradient: 0 to 50% [2M NH3 in methanol] in DCM) to afford 205 mg (93%) of 6-benzenesulfonyl-1-(4-methyl-piperidine-4-yl)1,6-dihydro-1,2,3,5,6-pentaaza-as-indacene. 1H NMR (400 MHz, DMSO): δ 9.25 (s, 1H), 8.19-8.17 (m, 3H), 7.76-7.72 (m, 1H), 7.65 (t, 2H), 7.48 (d, 1H), 2.83-2.80 (m, 4H), 2.55 (m, 2H), 2.00 (d, 2H), 1.82 (s, 3H).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe resulting residue purified by column chromatography (SCX-2, gradient: 0 to 50% [2M NH3 in methanol] in DCM)

Sources & evidence

ORD record
ord-bd38bc59cc004628a93e565754c51d3f
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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