Piperidine → HCID 178517182, compound

HRID 1615231Notes

Reaction equation

HRID 1615231 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[CH2:5]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:5]3/[C:6](=[O:11])[NH:7][C:8]4[C:4]/3=[CH:3][C:2]([F:1])=[CH:10][CH:9]=4)[CH:19]=2)[CH:14]=[N:13]1

Participants

5

Reactant 3

HCID 8082PiperidineHCID 37310125-fluoro-1,3-dihydro-2H-indol-2-oneHCID 185383681H-Indazole-6-carbaldehyde

Product 1

HCID 178517182HCID 178517182, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A scintillation vial was charged with 5-fluoroindolin-2-one (40 mg, 0.265 mmol), 1H-indazole-6-carbaldehyde (43 mg, 0.292 mmol), piperidine (3 uL, 0.027 mmol) and MeOH (2 mL). The reaction was then heated to 60° C. for 2 hrs. LC-MS analysis of the filtered yellow solid indicated a 9:1 mixture of geometric isomers. The mixture was resolved through prep-HPLC purification to give 11 mg, 15% of the major isomer (E) as the title compound. The minor fraction was also isolated; see Example A32. 1H NMR (400 MHz, d6-DMSO) δ 13.31 (s, 1H), 10.66 (s, 1H), 8.18 (s, 1H), 7.92 (d, J=8.7 Hz, 1H), 7.91 (s, 1H), 7.86 (s, 1H), 7.42 (d, J=8.5 Hz, 1H), 7.29 (d, J=9.5 Hz, 1H), 7.10 (t, J=6.8 Hz, 1H), 6.88 (dd, J1=8.8 Hz, J2=4.7, 1H); MS ESI 280.0 [M+H]+, calcd for [C16H10FN3O+H]+ 280.09.

Workup

  1. additiona 9:1 mixture of geometric isomers
  2. customThe mixture was resolved through prep-HPLC purification

Sources & evidence

ORD record
ord-d42fd64b49d64cd1a93ca2cd8527de17
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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