HCID 178451969, compound → HCID 178432024, compound

HRID 1257675Notes

Reaction equation

HRID 1257675 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][C:11]([CH3:26])([N:14]2[C:25]3[C:17](=[CH:18][N:19]=[C:20]4[C:24]=3[CH:23]=[CH:22][NH:21]4)[N:16]=[N:15]2)[CH2:10][CH2:9]1)=O)(C)(C)C>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH3:26][C:11]1([N:14]2[C:25]3[C:17](=[CH:18][N:19]=[C:20]4[C:24]=3[CH:23]=[CH:22][NH:21]4)[N:16]=[N:15]2)[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]1

Participants

3

Reactant 1

HCID 178451969HCID 178451969, compound

Product 1

HCID 178432024HCID 178432024, compoundYield 101%

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A mixture of 4-methyl-4-(6H-1,2,3,5,6-pentaaza-as-indacen-1-yl)-piperidine-1-carboxylic acid tert butyl ester (200 mg, 0.56 mmol) in DCM/TFA was stirred for 1.5 hours. The solvent was evaporated under vacuum and the resulting residue purified by column chromatography using an Isolute® SCX-2 column (gradient: 0 to 50% [2M NH3 in methanol] in DCM) to afford 145 mg (100%) of 1-(4-methyl-piperidin-4-yl)-1,6-dihydro-1,2,3,5,6-pentaaza-as-indacene. LCMS (Method I, ESI): RT=0.32 & 1.58 min, m+H=257.3; 1H NMR (400 MHz, DMSO) δ: 12.41 (s, 1H), 9.04 (s, 1H), 7.62 (d, 1H), 7.04 (m, 1H), 2.90 (m, 2H), 2.79 (m, 2H), 2.70 (m, 2H), 2.05 (m, 2H), 1.84 (s, 3H).

Workup

  1. customThe solvent was evaporated under vacuum
  2. customthe resulting residue purified by column chromatography

Sources & evidence

ORD record
ord-7ad9dffd48284736ae6f425187732549
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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