Hydrochloric Acid → HCID 178419906, compound

HRID 2114489Notes

Reaction equation

HRID 2114489 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:27]3[CH:26]=[CH:25][C:24]([C:28]4[NH:32][N:31]=[N:30][N:29]=4)=[CH:23][C:22]=3[O:21][C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]1)=O)(C)(C)C.Cl>CN(C=O)C>[NH:8]1[CH2:13][CH2:12][CH:11]([N:14]2[C:27]3[CH:26]=[CH:25][C:24]([C:28]4[NH:32][N:31]=[N:30][N:29]=4)=[CH:23][C:22]=3[O:21][C:20]3[C:15]2=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 178452046HCID 178452046, compound2×

Product 1

HCID 178419906HCID 178419906, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[3-(1H-tetrazol-5-yl)-phenoxazin-10-yl]-piperidine-1-carboxylic acid tert-butyl ester, 5a (0.265 g, 0.61 mmol) in DMF (2 mL) was added a 4N hydrochloric acid solution (4 mL). The mixture was stirred for 2 h at rt. Another 4 mL of the 4N HCl solution was added, and the mixture was stirred for 16 h at rt. The solvent was removed via evaporation, and the residue was purified via reverse phase chromatography (eluent gradient: 10 to 40% acetonitrile in water containing 0.1% TFA) to yield 0.12 g (44%) of 10-piperidin-4-yl-3-(1H-tetrazol-5-yl)-10H-phenoxazine, 6a as a TFA salt. MS m/z (MH+) 335.0.

Workup

  1. stirringthe mixture was stirred for 16 h at rt
  2. customThe solvent was removed via evaporation
  3. customthe residue was purified via reverse phase chromatography (eluent gradient: 10 to 40% acetonitrile in water containing 0.1% TFA)

Sources & evidence

ORD record
ord-b6514bda352a4f5b8865f2fd9eb04550
Source dataset
uspto-grants-2008_10
Patent number
US07432257B2

Reaction notes

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