M-Phenylenediamine → N-(2,5-Dimethyl-2H-pyrazol-3-ylmethyl)-2-[3-(pyrrol-1-yliminomethyl)-1H-indazol-6-ylamino]-benzamide

HRID 1827506Notes

Reaction equation

[CH3:1][N:2]1[C:6]([CH2:7][NH:8][C:9](=[O:41])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17]2[CH:25]=[C:24]3[C:20]([C:21]([CH:34]=[N:35][N:36]4[CH:40]=[CH:39][CH:38]=[CH:37]4)=[N:22][N:23]3COCC[Si](C)(C)C)=[CH:19][CH:18]=2)=[CH:5][C:4]([CH3:42])=[N:3]1.C1(N)C=CC=C(N)C=1>>[CH3:1][N:2]1[C:6]([CH2:7][NH:8][C:9](=[O:41])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[NH:16][C:17]2[CH:25]=[C:24]3[C:20]([C:21]([CH:34]=[N:35][N:36]4[CH:40]=[CH:39][CH:38]=[CH:37]4)=[N:22][NH:23]3)=[CH:19][CH:18]=2)=[CH:5][C:4]([CH3:42])=[N:3]1

Participants

Reactant 2

HCID 7935M-Phenylenediamine

HCID 69352972HCID 69352972, compound

Product 1

HCID 178426561N-(2,5-Dimethyl-2H-pyrazol-3-ylmethyl)-2-[3-(pyrrol-1-yliminomethyl)-1H-indazol-6-ylamino]-benzamide

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 that N-(2,5-Dimethyl-2H-pyrazol-3-ylmethyl)-2-[3-(pyrrol-1-yliminomethyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-indazol-6-ylamino]-benzamide was used 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 13.27 (1H, s), 9.72 (1H, s), 9.05 (1H, t, J=5.3 Hz), 8.97 (1H, s), 8.16 (1H, d, J=8.7 Hz), 7.68 (1H, dd, J=8.3, 1.9 Hz), 7.50 (2H, t, J=2.6 Hz), 7.46–7.38 (2H, m), 7.25 (1H, s), 7.05 (1H, dd, J=8.7, 1.9 Hz), 6.91 (1H, t, J=6.80 Hz), 6.20 (2H, t, J=2.3 Hz), 5.91 (1H, s), 4.43 (2H, d, J=5.6 Hz), 3.71 (3H, s), 2.04 (3H, s).

Workup

customPrepared in a similar manner to that

Sources & evidence

ORD record: ord-622cfa6a364042d38305d43f63556543
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07053107B2

Reaction notes

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