Hydrochloric Acid → HCID 57911413, compound

HRID 1099190Notes

Reaction equation

HRID 1099190 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]1[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C@H:20]2[C:26]3=[N:27][C:28](N)=[CH:29][CH:30]=[C:25]3[CH2:24][C@H:23]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=3[F:39])[CH2:22][CH2:21]2)=[O:18])[CH2:13][CH2:12]1.[ClH:40].[N+]([O-])([O-])=O.[Na+].[OH-].[Na+]>[Cu]Cl>[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]1[CH:11]1[CH2:16][CH2:15][N:14]([C:17]([O:19][C@H:20]2[C:26]3=[N:27][C:28]([Cl:40])=[CH:29][CH:30]=[C:25]3[CH2:24][C@H:23]([C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([F:38])[C:33]=3[F:39])[CH2:22][CH2:21]2)=[O:18])[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24268Sodium NitrateHCID 57911461HCID 57911461, compound

Product 1

HCID 57911413HCID 57911413, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

To the mixture of (6R,9R)-2-amino-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl 4-(2-oxo-2,3-dihydro-1H-imidazo[4,5-b]pyridin-1-yl)piperidine-1-carboxylate (45 mg, 0.084 mmol), HYDROCHLORIC ACID (3 mL, 36.5 mmol) was added COPPER(I) CHLORIDE (16.67 mg, 0.168 mmol) and SODIUM NITRATE (21.47 mg, 0.253 mmol) at −5° C. The reaction was stirred at this temperature for 1 hour and stirred at room temperature for 1 hour. NaOH (1N) was added to the reaction mixture before extract with ethyl acetate twice. The ethyl acetate layer was washed by brine before separated, dried (Na2SO4), filtered and concentrated. Flash column by methanol in CH2Cl2 from 0 to 4% to 8% to give the desired product (6.4 mg, 12%). MS (ESI)[M+H+]=554.09.

Workup

  1. stirringstirred at room temperature for 1 hour
  2. extractionbefore extract with ethyl acetate twice
  3. washThe ethyl acetate layer was washed by brine
  4. custombefore separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a10dc8ada16d4ddd9d980904b2de9d13
Source dataset
uspto-grants-2012_03
Patent number
US08143403B2

Reaction notes

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