Sodium triacetoxyborohydride → HCID 69177920, compound

HRID 899594Notes

Reaction equation

HRID 899594 reaction equation
[N:1]1[C:10]2[CH:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][N:16]3[C:24](=[O:25])[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]3=[O:26])[CH2:8][CH2:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[BH-](O[C:37]([CH3:39])=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[CH3:2][N:1]1[C:10]2[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=2[N:11]=[C:37]1[CH2:39][N:11]([CH:9]1[C:10]2[N:1]=[CH:2][CH:3]=[CH:4][C:5]=2[CH2:6][CH2:7][CH2:8]1)[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24](=[O:25])[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]1=[O:26]

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 589971372-[4-(5,6,7,8-Tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dione

Product 1

HCID 69177920HCID 69177920, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[4-(5,6,7,8-Tetrahydro-quinolin-8-ylamino)-butyl]-isoindole-1,3-dione (0.2011 g, 0.58 mmol) in dichloromethane (5.8 mL) was added 1-Methyl-1H-benoimidazole-2-carbaldehyde (0.1844 g, 1.15 mmol) and NaBH(OAc)3 (0.2462 g, 1.16 mmol), and was stirred at room temperature for four days. The organic phase was washed with NaHCO3 (2×10 mL), dried over Na2SO4, filtered, and concentrated. Purification of the crude material by column chromatography on silica gel (47:2:1 CH2Cl2-MeOH—NH4OH) provided 103 mg (36%) of 2-{4-[(1-Methyl-1H-benzoimidazol-2-ylmethyl)-(5,6,7,8-tetrahydro-quinolin-8-yl)-amino]-butyl}-isoindole-1,3-dione. 1H NMR (CDCl3) δ 1.30-1.44 (m, 2H), 1.48-1.63(m, 3H), 1.84-1.96 (m, 2H), 2.03-2.07 (m, 1H), 2.54-2.81 (m, 4H), 3.51 (t, 2H, J=7.2 Hz), 3.95 (s, 3H), 3.99-4.06 (m, 2H), 4.19 (d, 1H, J=13.5 Hz), 6.94-6.98 (m, 1H), 7.13-7.21 (m, 2H), 7.24-7.29 (m, 2H), 7.63-7.68 (m, 3H), 7.74-7.78 (m, 2H), 8.40 (d, 1H, J=3.6 Hz).

Workup

  1. washThe organic phase was washed with NaHCO3 (2×10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification of the crude material by column chromatography on silica gel (47:2:1 CH2Cl2-MeOH—NH4OH)

Sources & evidence

ORD record
ord-7069d09548894ce093fd4e6fe38e5ba4
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

Loading…