Piperidine → HCID 178507386, compound

HRID 1615271Notes

Reaction equation

HRID 1615271 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2.[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18]([CH:21]=O)[CH:19]=2)[CH:14]=[N:13]1.N1CCCCC1>CO>[NH:12]1[C:20]2[C:15](=[CH:16][CH:17]=[C:18](/[CH:21]=[C:7]3/[C:8](=[O:11])[NH:9][C:10]4[C:6]/3=[CH:5][CH:4]=[CH:3][C:2]=4[NH2:1])[CH:19]=2)[CH:14]=[N:13]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 64233127-aminoindolin-2-oneHCID 185383681H-Indazole-6-carbaldehyde

Product 1

HCID 178507386HCID 178507386, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A 13 mg (0.0877 mmol) solution of 7-aminooxindole (T. Nakashima & I. Suzuki, Chem. Pharm. Bull. (1969) 11, 2293) and 1H-indazole-6-carbaldehyde (14 mg, 0.0965 mmol) in MeOH (1.0 mL) was treated with piperidine (˜1 uL, 0.00877 mmol) and the reaction was heated to 60° C. for 4 hours. The MeOH was then removed in vacuo and the residue treated with 95:5 CH2Cl2/MeOH. The resulting precipitate was filtered and washed with 95:5 CH2Cl2/MeOH to obtain the title compound as a orange powder (6.7 mg, 28%). NMR (400 MHz, CD3OD) δ 8.14 (s, 1H), 7.94-7.87 (m, 3H), 7.46 (d, J=8.19 Hz, 1H), 7.31 (d, J=7.63 Hz, 1H), 6.90 (d, J=7.89 Hz, 1H), 6.81 (t, J=7.79 Hz, 1H); MS ESI 277.0 [M+H]+, calcd for [C16H12N4O+H]+ 277.11.

Workup

  1. customThe MeOH was then removed in vacuo
  2. additionthe residue treated with 95:5 CH2Cl2/MeOH
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with 95:5 CH2Cl2/MeOH

Sources & evidence

ORD record
ord-27743cb00f1742eb8ffe21ad0fee707c
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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