Acetic Acid → HCID 178477881, compound

HRID 2415609Notes

Reaction equation

[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][CH:13]3[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[N:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:23]=[C:22]([CH:30]=O)[CH:21]=1.C(O)(=O)C.C([BH3-])#N>ClC(Cl)C.CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([NH:12][C@H:13]3[CH2:14][CH2:15][C@@H:16]([NH:19][CH2:30][C:22]4[CH:21]=[N:20][C:29]5[C:24]([CH:23]=4)=[CH:25][CH:26]=[CH:27][CH:28]=5)[CH2:17][CH2:18]3)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution of N-(7-chloroquinolin-4-yl)-cyclohexane-1,4-diamine (40 mg, 0.14 mmol) and 3-quinolinecarboxaldehyde (22 mg, 0.14 mmol) in dichloroethane (0.5 mL) and methanol (0.5 mL) was treated acetic acid (0.018 mg, 0.28 mmol) and MP-cyanoborohydride (100 mg, 0.436 mmol, Argonaut Technologies). The mixture was stirred at 60° C. for 18 hours, filtered, and purified by reverse phase HPLC to provide the desired compound.

Workup

filtrationfiltered
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-24879b20a9004901b88d2ffdea53be1c
Source dataset: uspto-grants-2004_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06818772B2

Reaction notes

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