Piperidine → HCID 178517177, compound

HRID 1615228Notes

Reaction equation

HRID 1615228 reaction equation
[O:1]=[C:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:11]([NH:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[O:12])[CH:8]=2)[NH:3]1.[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26]([CH:29]=O)[CH:27]=2)[CH:22]=[N:21]1.N1CCCCC1>CO>[NH:20]1[C:28]2[C:23](=[CH:24][CH:25]=[C:26](/[CH:29]=[C:10]3/[C:2](=[O:1])[NH:3][C:4]4[C:9]/3=[CH:8][C:7]([C:11]([NH:13][C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)=[O:12])=[CH:6][CH:5]=4)[CH:27]=2)[CH:22]=[N:21]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 185383681H-Indazole-6-carbaldehydeHCID 68733542HCID 68733542, compound

Product 1

HCID 178517177HCID 178517177, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A scintillation vial was charged with 2-oxo-N-phenylindoline-5-carboxamide (22 mg, 0.087 mmol), 1H-indazole-6-carbaldehyde (14 mg, 0.096 mmol), piperidine (1 uL, 0.008 mmol) and MeOH (2 mL). The reaction was then heated to 60° C. for 2 hrs. A yellow precipitate formed which was further precipitated by cooling to room temperature and adding more MeOH (2 mL). The yellow solid was then filtered and washed with MeOH (10 mL) to give 8.0 mg, 24% of the title compound. 1H NMR (400 MHz, d6-DMSO) δ 13.42 (s, 1H), 11.02 (s, 1H), 10.16 (s, 1H), 9.01 (s, 1H), 8.39 (s, 1H), 8.14 (s, 2H), 8.03 (d, J=7.3 Hz, 1H), 7.89-7.82 (m, 2H), 7.79 (d, J=6.5 Hz, 2H), 7.36 (t, J=6.6 Hz, 2H), 7.11-7.09 (m, 1H), 6.96 (d, J=6.9 Hz, 1H); MS ESI 381.1 [M+H]+, calcd for [C23H16N4O2+H]+ 381.14.

Workup

  1. customA yellow precipitate formed which
  2. customwas further precipitated
  3. temperatureby cooling to room temperature
  4. additionadding more MeOH (2 mL)
  5. filtrationThe yellow solid was then filtered
  6. washwashed with MeOH (10 mL)

Sources & evidence

ORD record
ord-97de415c82a04d22839b3a687da05961
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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