Sodium cyanoborohydride → 2-[3-(2-tert-Butoxycarbonylmethoxy-3,5-dichlorobenzylamino)prop-1-ylamino]-1H-quinolin-4-one

HRID 430093Notes

Reaction equation

HRID 430093 reaction equation
C[O-].[Na+].[NH2:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[NH:10][C:11]2[C:16]([C:17](=[O:19])[CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2.[C:20]([O:24][C:25]([CH2:27][O:28][C:29]1[C:36]([Cl:37])=[CH:35][C:34]([Cl:38])=[CH:33][C:30]=1[CH:31]=O)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[NH3:4].[C:20]([O:24][C:25]([CH2:27][O:28][C:29]1[C:36]([Cl:37])=[CH:35][C:34]([Cl:38])=[CH:33][C:30]=1[CH2:31][NH:4][CH2:5][CH2:6][CH2:7][NH:8][C:9]1[NH:10][C:11]2[C:16]([C:17](=[O:19])[CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)=[O:26])([CH3:23])([CH3:21])[CH3:22]

Participants

8

Reactant 4

HCID 5003444Sodium cyanoborohydrideHCID 108569252-[(3-Aminopropyl)amino]-1,4-dihydroquinolin-4-oneHCID 10942334Sodium MethoxideHCID 183536852-Tert-butoxycarbonylmethoxy-3,5-dichlorobenzaldehyde

Product 2

HCID 222AmmoniaHCID 183537712-[3-(2-tert-Butoxycarbonylmethoxy-3,5-dichlorobenzylamino)prop-1-ylamino]-1H-quinolin-4-oneYield 158%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

To a solution of the compound prepared as in Example 1b (0.13 g, 0.45 mmol) in methanol (1 ml) and acetic acid (0.2 ml) was added sodium methoxide (0.5 M in methanol, 1.8 ml, 0.9 mmol). An aliquot of this solution (1.34 ml; 0.2 mmol 2-(3-aminoprop-1-ylamino)-1H-quinolin-4-one) was added to 2-tert-butoxycarbonylmethoxy-3,5-dichlorobenzaldehyde (0.061 g, 0.2 mmol) followed by sodium cyanoborohydride (0.02 g, 0.32 mmol) in methanol (0.6 ml). The mixture was stirred at room temperature under argon for 1 h. The product was purified by chromatography on a SCX cartridge, eluting with methanol and then 0.2M NH3 in methanol to give the title compound as a colourless gum (0.08 g, 79%); δH (CD3OD) 1.39 (9H, s), 1.8 (2H, m), 2.62 (2H, t), 3.33 (2H, t), 3.82 (2H, s), 4.52 (2H, s), 5.57 (1H, s), 7.1-7.5 (5H, m), and 7.99 (1H, dd): MS (ES+) 506, 508, 510 (12, 10, 3%, MH+), 450, 452 (10, 8%) and 201 (80).

Workup

  1. customThe product was purified by chromatography on a SCX cartridge
  2. washeluting with methanol

Sources & evidence

ORD record
ord-1881d06097bb4d08bca554c3fce412ac
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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