Diisopropylethylamine → HCID 68294839, compound

HRID 1854118Notes

Reaction equation

HRID 1854118 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-2ce5c0c6d6394067b3a051ff62ebcdee
Source dataset
uspto-grants-2015_02
Patent number
US08962620B2

Reaction notes

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