3,4-Dichlorobenzaldehyde → HCID 44458635, compound

HRID 430095Notes

Reaction equation

HRID 430095 reaction equation
Cl.Cl.[NH2:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][C@@H:5]1[CH2:9][NH:10][C:11]1[NH:12][C:13]2[C:18]([C:19](=[O:21])[CH:20]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH:26]=O.C([O-])(=O)C.[Na+].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[Cl:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][C:30]=1[Cl:31])[CH2:26][NH:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][C@@H:5]1[CH2:9][NH:10][C:11]1[NH:12][C:13]2[C:18]([C:19](=[O:21])[CH:20]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2

Participants

7

Reactant 4

HCID 227103,4-DichlorobenzaldehydeHCID 517045Sodium AcetateHCID 5003444Sodium cyanoborohydrideHCID 70248295HCID 70248295, compound

Product 1

HCID 44458635HCID 44458635, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

The title compound was prepared from 2-[((1R,2R)-2-aminocyclopentylmethyl)amino]-1H-quinolin-4-one dihydrochloride(0.059 g, 0.18 mmol), 3,4-dichlorobenzaldehyde (0.031 g, 0.18 mmol), sodium acetate (0.045 g, 0.54 mmol) and sodium cyanoborohydride (0.02 g, 0.32 mmol) in a 1% solution of acetic acid in methanol (2 mL) according to the procedure described in Example 61d. δH (CD3OD) 1.61-1.72 (3H, m), 1.79-1.96 (3H, m), 2.27-2.37 (1H, m), 3.18 (1H, q, J=6.44 Hz), 3.30 (1H, d×d, J=6.67 & 13.34 Hz), 3.49 (1H, d×d, J=6.95 & 13.28 Hz), 3.75 (1H, d, J=13.82 Hz), 3.88 (1H, d, J=13.76 Hz), 5.70 (1H, s), 7.18-7.32 (4H, m), 7.42 (1H, d, J=8.26 Hz), 7.51 (1H, t, J=7.84 Hz), 8.10 (1H, d, J=8.02 Hz). MS (ES+) 833 (5%) [2M]H+, 416 (87%) MH+.

Sources & evidence

ORD record
ord-210493ebe95a4aeea28985da7914d084
Source dataset
uspto-grants-2001_11
Patent number
US06320051B1

Reaction notes

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