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4-(N-Boc-amino)piperidine → HCID 68447292, compound

HRID 388956
Notes
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Reaction equation

HRID 388956 reaction equation
[NH2:1][C:2]1[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]([C:6]([NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[CH:11][CH:10]=2)=[O:7])=[C:4](Cl)[CH:3]=1.[C:24]([O:28][C:29](=[O:37])[NH:30][CH:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]1)([CH3:27])([CH3:26])[CH3:25]>CN1C(=O)CCC1.O>[C:24]([O:28][C:29](=[O:37])[NH:30][CH:31]1[CH2:36][CH2:35][N:34]([C:4]2[CH:3]=[C:2]([NH2:1])[C:19]([N+:20]([O-:22])=[O:21])=[CH:18][C:5]=2[C:6](=[O:7])[NH:8][C:9]2[CH:17]=[C:16]3[C:12]([CH:13]=[N:14][NH:15]3)=[CH:11][CH:10]=2)[CH2:33][CH2:32]1)([CH3:27])([CH3:25])[CH3:26]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 7238334-(N-Boc-amino)piperidineHCID 68443943HCID 68443943, compound

Product 1

HCID 68447292HCID 68447292, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
100 °C

Procedure

A solution 4-amino-2-chloro-N-(1H-indazol-6-yl)-5-nitrobenzamide (1 mmol; see Example 154) in NMP (2 mL) was added piperidin-4-yl-carbamic acid tert-butyl ester (4 mmol). The resulting mixture was heated at 100° C. for 10 h. The reaction mixture was cooled to room temperature, and diluted with water (20 mL). The solid formed was collected by filtration, washed with water, and dried in vacuo. The crude product was purified on a silica gel column chromatography using EtOAc/hexane as eluent to provide {1-[5-Amino-2-(1H-indazol-6-ylcarbamoyl)-4-nitro-phenyl]-piperidin-4-yl}-carbamic acid tert-butyl ester as a light yellow solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customThe solid formed
  3. filtrationwas collected by filtration
  4. washwashed with water
  5. customdried in vacuo
  6. customThe crude product was purified on a silica gel column chromatography

Sources & evidence

ORD record
ord-f329fa8706ba4c1e9ea9232c16b1bad8
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08377983B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes