Dimethylformamide → HCID 131726489, compound

HRID 1766616Notes

Reaction equation

[CH2:1]([C:3]1[N:11]=[C:10]([O:12][CH3:13])[C:9]([NH:14][C:15]([N:17]2[CH2:22][CH2:21][N:20]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19][CH2:18]2)=[O:16])=[CH:8][C:4]=1[C:5](O)=[O:6])[CH3:2].C1C=CC2N([OH:38])N=NC=2C=1.[CH:39]1[C:52]2[C:43](=[N:44][C:45]3[C:50]([C:51]=2[NH:53][C:54]2[CH:55]=[C:56]([CH2:61]O)C=C(N)[CH:59]=2)=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:42]=[CH:41][CH:40]=1.C[N:64]([CH:66]=O)[CH3:65]>>[CH:49]1[C:50]2[C:45](=[N:44][C:43]3[C:52]([C:51]=2[NH:53][C:54]2[CH:59]=[C:66]([N:64]([CH3:65])[C:5]([C:4]4[CH:8]=[C:9]([NH:14][C:15]([N:17]5[CH2:18][CH2:19][N:20]([C:23]6[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=6)[CH2:21][CH2:22]5)=[O:16])[C:10]([O:12][CH3:13])=[N:11][C:3]=4[CH2:1][CH3:2])=[O:6])[CH:61]=[C:56]([OH:38])[CH:55]=2)=[CH:39][CH:40]=[CH:41][CH:42]=3)[CH:46]=[CH:47][CH:48]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 757711-Hydroxybenzotriazole

HCID 3804823-(9-Acridinylamino)-5-hydroxymethylaniline

HCID 21111627HCID 21111627, compound

Product 1

HCID 131726489HCID 131726489, compoundYield 73.2%

Procedure

2-ethyl-6-methoxy-5-[(4-phenylpiperazine-1-carbonyl)amino]nicotinic acid (6.48 g, 15.7 mmole) was dissolved in DMF (100 mL), thereto WSCD (3 g, 15.7 mmole) HOBT (2.12g, 15.7 mmole) and [3-(acridine-9-yl-amino)-5-aminophenyl]-methanol were added. The resulting mixture was stirred for 24 hours at the room temperature and the solvent used was removed under the reduced pressure. Then, the resulting product was purified by column chromatography to give the titled compound.

Workup

customthe solvent used was removed under the reduced pressure
customThen, the resulting product was purified by column chromatography

Sources & evidence

ORD record: ord-e013b2a6740d415da994d25d79d74bac
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07230105B2

Reaction notes

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