M-Phenylenediamine → HCID 11433014, compound

HRID 270713Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Cl:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:28])[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)=[CH:12][C:11]=1[C:29]1[C:42](=[O:43])[N:41]([CH3:44])[C:32]2[N:33]=[C:34](S(C)(=O)=O)[N:35]=[CH:36][C:31]=2[CH:30]=1>CO>[NH2:1][C:2]1[CH:3]=[C:4]([NH:5][C:34]2[N:35]=[CH:36][C:31]3[CH:30]=[C:29]([C:11]4[CH:12]=[C:13]([NH:16][C:17](=[O:28])[C:18]5[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:26])([F:25])[F:27])[CH:19]=5)[CH:14]=[CH:15][C:10]=4[Cl:9])[C:42](=[O:43])[N:41]([CH3:44])[C:32]=3[N:33]=2)[CH:6]=[CH:7][CH:8]=1

Participants

Conditions

Temperature: 110 °C

Procedure

3-Aminoaniline (121.1 mg, 1.12 mmonl) is heated to 110° C. When melted, N-[4-chloro-3-(2-methanesulfonyl-8-methyl-7-oxo-7,8-dihydro-pyrido[2,3-d]pyrimidin-6-yl)-phenyl]-3-trifluoromethyl-benzamide 34 (15 mg, 0.028 mmol) is added. The reaction is stirred at 110° C. for 25 minutes. The reaction is diluted with MeOH (1 mL) and purified by prep-HPLC to give the final product as a yellow solid: 1H NMR (CDCl3): δ3.64 (s, 3H), 6.66 (d, 1H), 7.17 (t, 1H), 7.28 (d, 1H), 7.42 (m, 2H), 7.48 (t, 1H), 7.50 (dd, 1H), 7.57 (s, 1H), 7.63 (m, 2H), 7.97 (d, 1H), 8.07 (s, 1H), 8.49 (s, 1H); MS m/z 565.0 (M+1).

Workup

custompurified by prep-HPLC

Sources & evidence

ORD record: ord-c93c1f22b1a7427e8766ce5175d51384
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07449582B2

Reaction notes

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