Diisopropylethylamine → HCID 68294839, compound

HRID 1909300Notes

Reaction equation

HRID 1909300 reaction equation
[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([C:15]4[O:16][C:17]([CH:20]=O)=[CH:18][CH:19]=4)[CH:11]=[C:10]([C:22]([NH:24][CH2:25][C:26]4[C:27](=[O:34])[NH:28][C:29]([CH3:33])=[CH:30][C:31]=4[CH3:32])=[O:23])[C:9]=3[CH:8]=[N:7]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:35][S:36]([CH2:39][CH2:40][NH2:41])(=[O:38])=[O:37].CCN(C(C)C)C(C)C.[BH3-]C#N.[Na+]>CO>[CH:1]1([N:6]2[C:14]3[CH:13]=[C:12]([C:15]4[O:16][C:17]([CH2:20][NH:41][CH2:40][CH2:39][S:36]([CH3:35])(=[O:38])=[O:37])=[CH:18][CH:19]=4)[CH:11]=[C:10]([C:22]([NH:24][CH2:25][C:26]4[C:27](=[O:34])[NH:28][C:29]([CH3:33])=[CH:30][C:31]=4[CH3:32])=[O:23])[C:9]=3[CH:8]=[N:7]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 43405612-(Methylsulfonyl)ethanamineHCID 5003444Sodium cyanoborohydrideHCID 86703439HCID 86703439, compound

Product 1

HCID 68294839HCID 68294839, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)-methyl)-6-(5-formylfuran-2yl)-1H-indazole-4-carboxamide (0.09 g, 0.19 mmol) in methanol (2 mL), 2-(methylsulfonyl)ethanamine (0.072 g, 0.581 mmol) and DIPEA (0.05 g, 0.39 mmol) was added at room temperature and reaction stirred for 3 h. Then NaBH3CN (0.012 g, 0.196 mmol) was added and reaction stirred at room temperature for 18 h. On completion, methanol was removed under reduced pressure and then water was added to the residue. The aqueous phase was extracted with 10% MeOH/DCM and the combined organic layers were dried over sodium sulfate and concentrated to obtain crude material which was purified by column chromatography to afford 1-cyclopentyl-N-((4,6-dimethyl-2-oxo-1,2-dihydropyridin-3-yl)methyl)-6-(5-(((2-(methylsulfonyl)ethyl)amino)methyl)furan-2-yl)-1H-indazole-4-carboxamide. LCMS: 566.90 (M+1)+; HPLC: 90.05% (@ 254 nm) (Rt;5.253); 1H NMR (MeOD, 400 MHz) δ 8.31 (s, 1H), 8.07 (s, 1H), 7.87 (s, 1H), 6.92 (s, 1H), 6.44 (s, 1H), 6.13 (s, 1H), 5.18-5.42 (m, 1H), 4.59 (s, 2H), 4.57 (s, 2H), 3.91 (s, 2H), 3.16 (t, 2H, J=6.4 Hz), 3.02 (s, 3H), 2.42 (s, 3H), 2.25 (s, 3H), 2.19-2.23 (m, 2H), 2.11-2.14 (m, 2H), 1.98 (m, 2H), 1.80 (m, 2H).

Workup

  1. customreaction
  2. customreaction
  3. stirringstirred at room temperature for 18 h
  4. customOn completion, methanol was removed under reduced pressure
  5. additionwater was added to the residue
  6. extractionThe aqueous phase was extracted with 10% MeOH/DCM
  7. dry with materialthe combined organic layers were dried over sodium sulfate
  8. concentrationconcentrated
  9. customto obtain crude material which
  10. customwas purified by column chromatography

Sources & evidence

ORD record
ord-9e3a9aba113a4eb8b72cb0c88dbb1709
Source dataset
uspto-grants-2013_12
Patent number
US08598167B1

Reaction notes

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