M-Phenylenediamine → HCID 178524308, compound

HRID 1827507Notes

Reaction equation

[N:1]1([N:6]=[CH:7][C:8]2[C:16]3[C:11](=[CH:12][C:13]([NH:17][C:18]4[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=4[C:20]([OH:22])=[O:21])=[CH:14][CH:15]=3)[N:10](COCC[Si](C)(C)C)[N:9]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1.C1(N)C=CC=C(N)C=1>>[N:1]1([N:6]=[CH:7][C:8]2[C:16]3[C:11](=[CH:12][C:13]([NH:17][C:18]4[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=4[C:20]([OH:22])=[O:21])=[CH:14][CH:15]=3)[NH:10][N:9]=2)[CH:5]=[CH:4][CH:3]=[CH:2]1

Participants

Reactant 2

HCID 7935M-Phenylenediamine

HCID 69353167HCID 69353167, compound

Product 1

HCID 178524308HCID 178524308, compound

Procedure

Prepared in a similar manner to that described for Example 11 in U.S. Pat. No. 6,534,524, issued Mar. 18, 2003, herein incorporated by reference in its entirety for all purposes, except using 2-[3-(Pyrrol-1-yliminomethyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-6-ylamino]-benzoic acid instead of N-methyl-N-{3-styryl-1-[2-trimethyl-silanyl)-ethoxymethyl]-1H-indazol-6-yl}-benzene-1,3-diamine. 1H NMR (DMSO-d6) δ 13.12 (1H, s), 12.70 (1H, s), 8.94 (1H, s), 8.10 (1H, d, J=8.7 Hz), 7.91 (1H, dd, J=1.7, 7.7 Hz), 7.50 (2H, t, J=2.3 Hz), 7.36 (1H, d, J=7.9 Hz), 7.27 (1H, d, J=1.5 Hz), 7.16 (1H, t, J=7.5 Hz), 6.94 (1H, dd, J=1.7, 8.7 Hz), 6.68 (1H, t, J=7.5 Hz), 6.19(2H, t, J=2.3 Hz).

Workup

customPrepared in a similar manner to that

Sources & evidence

ORD record: ord-fb76f0713c4b4475ac25a7eadadf4ae8
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053107B2

Reaction notes

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