Methanol → HCID 66796016, compound

HRID 1944817Notes

Reaction equation

HRID 1944817 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]([CH:31]([CH3:33])[CH3:32])=[CH:29][CH:28]=[CH:27][C:26]=2[CH:34]([CH3:36])[CH3:35])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2].CO.[BH3-]C#N.[Na+]>C(O)=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]([CH:31]([CH3:32])[CH3:33])=[CH:29][CH:28]=[CH:27][C:26]=2[CH:34]([CH3:36])[CH3:35])[CH:20]=[CH:19][CH:18]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 887MethanolHCID 5003444Sodium cyanoborohydrideHCID 66795703HCID 66795703, compound

Product 1

HCID 66796016HCID 66796016, compound

Reagents, catalysts & solvents 2

HCID 284Formic AcidCatalystHCID 962WaterSolvent

Procedure

To a solution of 2.45 g (5.10 mmol) of N-[(6-{2-[(tert-butylamino) methyl]-1-naphthyl}pyridin-2-yl)methylene]-2,6-diisopropylaniline in 50 ml of hot methanol 0.53 g (8.40 mmol) of NaBH3CN was added in one portion followed by the addition of four drops of 88% formic acid. The resulting 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 combined extract was washed by 2×50 ml of 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=100:5:1, vol.). Yield 1.60 g (65%) of orange oil. Anal. calc. for C33H41N3: C, 82.63; H, 8.61; N, 8.76. Found: C, 82.74; H, 8.79; N, 8.60. 1H NMR (CDCl3): 7.89 (d, J=8.3 Hz, 1H, 4-H in naphthyl), 7.86 (m, 1H, 8-H in naphthyl), 7.82 (m, 1H, 4-H in Py), 7.65 (d, J=8.3 Hz, 1H, 3-H in naphthyl), 7.47 (m, 11-1, 3-H in Py), 7.44 (m, 1H, 7-H in naphthyl), 7.33-7.40 (m, 3H, 5-H in Py and 5,6-H in naphthyl), 7.04-7.11 (m, 3H, 3,4,5-H in Ph), 4.37 (d, J=14.7 Hz, 1H, CHH′N′Bu), 4.25 (d, J=14.7 Hz, 1H, CHH′NtBu), 3.56 (m, 2H, CH2NAr), 3.33 (sept, J=7.1 Hz, 2H, CH2Me2), 2.04 (s, 1H, NHAr), 1.18 (d, J=7.1 Hz, 6H, CHMeMe'), 1.16 (d, J=7.1 Hz, 6H, CHMeMe′), 0.96 (s, 9H, tBu).

Workup

  1. temperatureThe resulting mixture was refluxed under inert atmosphere for 1 hour
  2. extractionThe crude product was extracted with 3×20 ml of ether
  3. extractionThe combined extract
  4. washwas washed by 2×50 ml of 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=100:5:1, vol.)

Sources & evidence

ORD record
ord-76d4696d3bb64e7dbc19d051802ff0c6
Source dataset
uspto-grants-2013_03
Patent number
US08394902B2

Reaction notes

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