1-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acid → HCID 22479820, compound

HRID 1353846Notes

Reaction equation

HRID 1353846 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.[NH2:29][C:30]1[CH:31]=[C:32]([C:36]2[C:44]3[C:39](=[CH:40][CH:41]=[C:42]([C:45]#[N:46])[CH:43]=3)[N:38]([CH:47]3[CH2:52][CH2:51][CH2:50][CH2:49][O:48]3)[N:37]=2)[CH:33]=[CH:34][CH:35]=1>ClCCl>[C:45]([C:42]1[CH:43]=[C:44]2[C:39](=[CH:40][CH:41]=1)[N:38]([CH:47]1[CH2:52][CH2:51][CH2:50][CH2:49][O:48]1)[N:37]=[C:36]2[C:32]1[CH:31]=[C:30]([NH:29][C:14]([CH:11]2[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH2:12]2)=[O:16])[CH:35]=[CH:34][CH:33]=1)#[N:46]

Participants

5

Reactant 3

HCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride2×HCID 22480146HCID 22480146, compound

Product 1

HCID 22479820HCID 22479820, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 1-[(tert-butyl)oxycarbonyl]piperidine-4-carboxylic acid (0.317 g, 1.38 mmol) in 12 mL of dichloromethane was added 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) (0.287 g, 1.5 mmol). The solution was stirred at room temperature for 10 min before 3-(3-aminophenyl)-1-perhydro-2H-pyran-2-yl-1H-indazole-5-carbonitrile (0.400 g, 1.25 mmol) was added as a solid. (A small volume of dichloromethane was used to rinse the flask containing the core). The reaction was stirred at room temperature for 12 hours. Even after addition of 0.5 equivalent of carboxylic acid and EDCI, the reaction could not be driven to completion. The crude mixture was partitioned between water and dichloromethane. The crude was isolated as a brown oil. The yield was not calculated.

Workup

  1. additionwas added as a solid
  2. washto rinse the flask
  3. additioncontaining the core)
  4. customthe reaction could not
  5. customThe crude mixture was partitioned between water and dichloromethane
  6. customThe crude was isolated as a brown oil

Sources & evidence

ORD record
ord-f25226b93aa74bb397fc75b01f277577
Source dataset
uspto-grants-2007_05
Patent number
US07220771B2

Reaction notes

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