Ethyl orthoformate → HCID 22238160, compound

HRID 2117350Notes

Reaction equation

[NH2:1][C:2]1[C:32]([N:33]([CH2:35][CH2:36][CH2:37][N:38]([CH3:40])[CH3:39])[CH3:34])=[CH:31][CH:30]=[CH:29][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[C:9]([CH:26]=[CH:27][CH:28]=1)[C:10]([NH:12][C:13]1[CH:18]=[C:17]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:16]=[C:15]([F:25])[CH:14]=1)=[O:11])=[O:5].[CH:41](OCC)(OCC)OCC>>[F:25][C:15]1[CH:14]=[C:13]([NH:12][C:10]([C:9]2[CH:8]=[C:7]([N:6]3[C:4](=[O:5])[C:3]4[C:2](=[C:32]([N:33]([CH2:35][CH2:36][CH2:37][N:38]([CH3:39])[CH3:40])[CH3:34])[CH:31]=[CH:30][CH:29]=4)[N:1]=[CH:41]3)[CH:28]=[CH:27][CH:26]=2)=[O:11])[CH:18]=[C:17]([N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[CH:16]=1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 22238153HCID 22238153, compound

Product 1

HCID 22238160HCID 22238160, compound

Procedure

Using an analogous procedure to that described in Example 1, 3-{2-amino-3-[N-(3-dimethylaminopropyl)-N-methylamino]benzamido]-N-(3-fluoro-5-morpholinophenyl)benzamide was reacted with triethyl orthoformate. The reaction product was purified by column chromatography on an isolute SCX ion exchange column using initially methanol and then a 99:1 mixture of methanol and a saturated aqueous ammonium hydroxide solution as eluent. There was thus obtained the title compound Mass Spectrum: M+H+559.

Workup

customThe reaction product was purified by column chromatography on an isolute SCX ion exchange column
additiona 99:1 mixture of methanol

Sources & evidence

ORD record: ord-b7c86e0d7325490fbd75ed54e16652db
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442704B2

Reaction notes

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