Acetic Acid → N-{1-[3-(3-methylpiperidin-1-yl)propyl]-1H-indazol-6-yl}-2-(4-phenoxyphenyl)acetamide

HRID 1790150Notes

Reaction equation

HRID 1790150 reaction equation
O=[CH:2][CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15](=[O:30])[CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[CH:19][CH:18]=3)[CH:12]=2)[CH:7]=[N:6]1.[CH3:31][CH:32]1[CH2:37][CH2:36][CH2:35][NH:34][CH2:33]1.C(O)(=O)C>CO>[CH3:31][CH:32]1[CH2:37][CH2:36][CH2:35][N:34]([CH2:2][CH2:3][CH2:4][N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([NH:14][C:15](=[O:30])[CH2:16][C:17]4[CH:18]=[CH:19][C:20]([O:23][C:24]5[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=5)=[CH:21][CH:22]=4)[CH:12]=3)[CH:7]=[N:6]2)[CH2:33]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 790813-MethylpiperidineHCID 22036564N-[1-(3-oxopropyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide

Product 1

HCID 11225432N-{1-[3-(3-methylpiperidin-1-yl)propyl]-1H-indazol-6-yl}-2-(4-phenoxyphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of N-[1-(3-oxopropyl)-1H-indazol-6-yl]-2-(4-phenoxyphenyl)acetamide (20 mg, 0.05 mmol) and 3-methylpiperidine (10 mg, 0.10 mmol) in methanol containing 2% v/v acetic acid (1 mL) was added and MP-CNBH3 (52 mg, 0.065 mmol). The mixture was shaken at 40 C for 18 hours, cooled to room temperature and filtered, eluting with additional methanol (3×0.5 mL). The filtrate was concentrated under reduced pressure and was purified by RP-HPLC to provide the title compound. 1H NMR (300 MHz, DMSO-D6) δ ppm 0.85 (d, J=6.44 Hz, 3 H), 0.99 (m, 1H), 1.71 (m, 4 H), 2.26 (m, 2H,) 2.73 (m, 1 H), 3.06 (m, 2 H), 3.35 (m, 3 H), 3.69 (s, 2 H), 4.38 (t, J=6.95 Hz, 2 H), 6.99 (m, 4 H), 7.10 (m, 2 H), 7.39 (m, 4 H), 7.69 (m, 1 H), 8.01 (s, 1 H), 8.26 (s, 1 H), and 10.39 (s, 1 H); MS (ESI) 483 (M+H)+.

Workup

  1. additionwas added
  2. filtrationfiltered
  3. washeluting with additional methanol (3×0.5 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customwas purified by RP-HPLC

Sources & evidence

ORD record
ord-2e4a8dd9a6bf48d4bfe72c30037c6410
Source dataset
uspto-grants-2006_07
Patent number
US07071182B2

Reaction notes

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