Hydrochloric Acid → tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate

HRID 655938Notes

Reaction equation

HRID 655938 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH:28]=[C:27]4[C:22]([C:23]([C:29](O)=[O:30])=[CH:24][CH:25]=[CH:26]4)=[N:21]3)=[CH:16][CH:15]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)(OC(C)(C)C)OC(C)(C)C.[N:44]1C=CC=CC=1.C(=O)(O)[O-].[NH4+].Cl>C(Cl)Cl>[NH2:44][C:29]([C:23]1[C:22]2[C:27](=[CH:28][N:20]([C:17]3[CH:18]=[CH:19][C:14]([C@@H:10]4[CH2:11][CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])[CH2:9]4)=[CH:15][CH:16]=3)[N:21]=2)[CH:26]=[CH:25][CH:24]=1)=[O:30]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 14013Ammonium BicarbonateHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 57501623(S)-2-(4-(1-(tert-butoxycarbonyl)piperidin-3-yl)phenyl)-2H-indazole-7-carboxylicacid

Product 1

HCID 44550022tert-butyl (3S)-3-{4-[7-(aminocarbonyl)-2H-indazol-2-yl]phenyl}piperidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

F2 was dissolved in DCM (0.35M) and di tert-butyl carbonate (1.3 eq) and pyridine (1.0 eq) added at RT. After 30 minutes ammonium bicarbonate (1.3 eq) was added and stirring continued for 20 hours. 1M HCl (5 mL/g) was added and the phases separated, the organic layer was washed twice with water and concentrated to a low volume. The crude compound (F3) was filtered through a pad of silica and then crystallised from methyl tert-butyl ether.

Workup

  1. customthe phases separated
  2. washthe organic layer was washed twice with water
  3. concentrationconcentrated to a low volume
  4. filtrationThe crude compound (F3) was filtered through a pad of silica
  5. customcrystallised from methyl tert-butyl ether

Sources & evidence

ORD record
ord-f4f5a46a3ed344b382b2986d31a4b597
Source dataset
uspto-grants-2011_12
Patent number
US08071623B2

Reaction notes

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