Ethyl orthoformate → HCID 53690208, compound

HRID 2117353Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:23])[C:10]2[CH:15]=[C:14]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH:13]=[C:12]([F:22])[CH:11]=2)=[CH:4][C:3]=1[NH:24][C:25](=[O:41])[C:26]1[CH:31]=[C:30]([N:32]2[CH2:38][CH2:37][CH2:36][N:35]([CH3:39])[CH2:34][CH2:33]2)[CH:29]=[CH:28][C:27]=1[NH2:40].[CH:42](OCC)(OCC)OCC>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:23])[C:10]2[CH:15]=[C:14]([N:16]3[CH2:17][CH2:18][O:19][CH2:20][CH2:21]3)[CH:13]=[C:12]([F:22])[CH:11]=2)=[CH:4][C:3]=1[N:24]1[C:25](=[O:41])[C:26]2[C:27](=[CH:28][CH:29]=[C:30]([N:32]3[CH2:38][CH2:37][CH2:36][N:35]([CH3:39])[CH2:34][CH2:33]3)[CH:31]=2)[N:40]=[CH:42]1

Participants

Reactant 2

HCID 31214Ethyl orthoformate

HCID 22238210HCID 22238210, compound

Product 1

HCID 53690208HCID 53690208, compoundYield 63%

Procedure

Using an analogous procedure to that described in Example 18, N-[2-fluoro-5-(3-fluoro-5-morpholinobenzamido)phenyl]-2-amino-5-(4-methylhomopiperazin-1-yl)benzamide was reacted with triethyl orthoformate to give the title compound in 63% yield; NMR Spectrum: (DMSOd6) 1.92 (m, 2H), 2.25 (s, 3H), 2.46 (m, 2H), 2.64 (m, 2H), 3.21 (t, 4H), 3.53 (t, 2H), 3.6 (m, 2H), 3.72 (t, 4H), 6.99 (d, 1H), 7.12 (d, 1H), 7.23 (m, 1H), 7.3 (s, 1H), 7.36 (m, 1H), 7.48 (t, 1H), 7.58 (d, 1H), 7.87 (m, 1H), 7.96 (m, 1H), 8.06 (s, 1H), 10.43 (s, 1H); Mass Spectrum: M+H+575.

Sources & evidence

ORD record: ord-2823f7ae27764f5db81764dc96b90a3b
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07442704B2

Reaction notes

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