2-Pyridinecarboxaldehyde → HCID 68790113, compound

HRID 628680Notes

Reaction equation

HRID 628680 reaction equation
[ClH:1].Cl.Cl.Cl.[NH2:5][CH2:6][CH2:7][CH2:8][CH2:9][N:10]([CH2:21][C:22]1[N:23]=[N:24][N:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH:26]=1)[CH:11]1[C:20]2[N:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:14][CH2:13][CH2:12]1.CCN(C(C)C)C(C)C.[N:42]1[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=1[CH:48]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(O)(=O)C>[ClH:1].[C:27]1([N:25]2[CH:26]=[C:22]([CH2:21][N:10]([CH:11]3[C:20]4[N:19]=[CH:18][CH:17]=[CH:16][C:15]=4[CH2:14][CH2:13][CH2:12]3)[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][CH2:48][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][N:42]=3)[N:23]=[N:24]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 5

HCID 142732-PyridinecarboxaldehydeHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 68732742HCID 68732742, compound

Product 1

HCID 68790113HCID 68790113, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
65 °C

Procedure

A solution of N-(4-aminobutyl)-N-((1-phenyl-1H-1,2,3-triazol-4-yl)methyl)-5,6,7,8-tetrahydro-quinolin-8-amine tetrahydrochloride, Z, (0.20 g, 0.38 mmol) in 1,2-dichloroethane (10 mL) was treated with Hünigs base (0.08 mL, 0.42 mmol), 2-pyridine carboxaldehyde (0.04 mL, 0.42 mmol), sodium triacetoxyborohydride (0.12 g, 0.57 mmol) and a catalytic amount of acetic acid (2 drops). The resulting mixture was warmed to 65° C. and stirred for 18 h. The reaction mixture was cooled to room temperature. A saturated aqueous solution of sodium bicarbonate was added. The product was extracted with dichloromethane. The combined organic layers were washed with brine, dried over potassium carbonate, filtered and concentrated in vacuo. The crude product was purified by silica gel chromatography (0-15% methanol/CH2Cl2) to afford 0.08 g (45% yield) of the desired product AB: 1H NMR (400 MHz, CDCl3) δ 8.54-8.34 (m, 2H), 8.15 (bs, 1H), 7.71 (d, J=7.6 Hz, 1H), 7.60-7.52 (m, 1H), 7.45 (t, J=7.2 Hz, 2H), 7.39-7.32 (m, 1H), 7.32-7.22 (m, 2H), 7.14-7.04 (m, 1H), 7.02-6.84 (m, 1H), 4.15-4.04 (m, 1H), 3.92-3.70 (m, 4H), 2.82-2.50 (m, 6H), 2.15-2.04 (m, 1H), 2.04-1.82 (m, 1H), 1.82-1.78 (m, 1H), 1.70-1.40 (m, 5H); ESI+ MS: m/z (rel intensity) 468.3 (100, [M+H]+).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe product was extracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over potassium carbonate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by silica gel chromatography (0-15% methanol/CH2Cl2)

Sources & evidence

ORD record
ord-5b7493647e054be597428033d93ffe4d
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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