Water → HCID 66795949, compound

HRID 1944814Notes

Reaction equation

HRID 1944814 reaction equation
[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH:23]=[N:24][C:25]2[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][C:26]=2[CH3:33])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].[BH3-]C#N.[Na+].O>CO.C(O)=O>[C:1]([NH:5][CH2:6][C:7]1[CH:16]=[CH:15][C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]=1[C:17]1[N:22]=[C:21]([CH2:23][NH:24][C:25]2[C:30]([CH3:31])=[CH:29][C:28]([CH3:32])=[CH:27][C:26]=2[CH3:33])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 66795765HCID 66795765, compound

Product 1

HCID 66795949HCID 66795949, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1.75 g (4.10 mmol) of N-[(6-{2-[(tert-butylamino)methyl]-1-naphthyl}pyridin-2-yl)methylene]-2,4,6-trimethylaniline in 20 ml of methanol, 0.42 g (6.70 mmol) of NaBH3CN was added in one portion followed by addition of three drops of 88% formic acid. The reaction mixture was refluxed under inert atmosphere for 1 hour and then poured into 50 ml of water. The crude product was extracted with 3×20 ml of ether. The organic extract was washed with water, dried over K2CO3, and then evaporated to dryness. The product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-methanol-triethylamine=100:10:1, vol.). Yield 1.60 g (90%) of orange oil. Anal. calc. for C30H35N3: C, 82.34; H, 8.06; N, 9.60. Found: C, 82.56; H, 8.21; N, 9.59. 1H NMR (CDCl3): 7.89 (d, J=8.5 Hz, 1H, 4-H in naphthyl), 7.86 (m, 1H, 8-H in naphthyl), 7.77 (m, 1H, 4-H in Py), 7.65 (d, J=8.5 Hz, 3-H in naphthyl), 7.43 (m, 1H, 7-H in naphthyl)), 7.87 (m, 1H, 3-H in Py), 7.30-7.35 (m, 3H, 5-H in Py and 5,6-H in naphthyl), 6.80 (s, 2H, 3,5-H in mesityl), 4.35 (m, 2H, CH2NHtBu), 3.55 (m, 2H, CH2NMes), 2.94 (br. s, 2H, NH), 2.24 (s, 6H, 2,6-Me in mesityl), 2.22 (s, 3H, 4-Me in mesityl), 0.96 (s, 9H, tBu).

Workup

  1. temperatureThe reaction mixture was refluxed under inert atmosphere for 1 hour
  2. extractionThe crude product was extracted with 3×20 ml of ether
  3. extractionThe organic extract
  4. washwas washed with water
  5. dry with materialdried over K2CO3
  6. customevaporated to dryness
  7. customThe product was isolated by flash chromatography on silica gel 60 (40-63 um; eluent: dichloromethane-methanol-triethylamine=100:10:1, vol.)

Sources & evidence

ORD record
ord-e5158f4cd22d48a88c25a98d2730a6c6
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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