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

HRID 388956Notes

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]

Participants

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

temperatureThe reaction mixture was cooled to room temperature
customThe solid formed
filtrationwas collected by filtration
washwashed with water
customdried in vacuo
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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