Ammonia → N-[4-(2-Amino-6-methylpyrimidin-4-ylamino)phenyl]-4-nitrobenzamide

HRID 547528Notes

Reaction equation

[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CC=CC=1.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH:26][C:27]2[CH:32]=[C:31]([CH3:33])[N:30]=[C:29]([NH2:34])[N:28]=2)=[CH:22][CH:21]=1.N>O1CCOCC1>[NH2:34][C:29]1[N:28]=[C:27]([NH:26][C:23]2[CH:24]=[CH:25][C:20]([NH:19][C:8](=[O:9])[C:7]3[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)=[CH:21][CH:22]=2)[CH:32]=[C:31]([CH3:33])[N:30]=1

Participants

Conditions

Temperature: 50 °C

Procedure

4-Nitrobenzoyl chloride (11.00 g, 0.06 mol) and dry pyridine (9.08 mL, 0.11 mol) were sequentially added to a solution of amine E3 (4.85 g, 0.02 mol) in dry dioxane (200 mL), and the resulting solution heated at ˜50° C. for 5 d. After this time, the reaction mixture was cooled to room temperature, and then basified by addition of aqueous ammonia solution. The resulting suspension was filtered through a pad of Celite to afford amide E4 as an amorphous yellow solid (3.40 g, 41%). 1H NMR [(CD3)2SO]: 2.09 [s, 3H, ArCH3], 5.87 [s, 1H, ArNHAr], 6.08 [br s, 6.08, ArNH2], 7.68 [m, 4H, ArH], 8.18 [d, J=8.80 Hz, 2H, ArH], 8.36 [d, J=8.80 Hz, 2H, ArH], 8.95 [s, 1H, ArH], 10.45 [s, 1H, ArC(O)NHAr]. LCMS (APCI+): 365 (100%).

Workup

temperatureAfter this time, the reaction mixture was cooled to room temperature
filtrationThe resulting suspension was filtered through a pad of Celite

Sources & evidence

ORD record: ord-0a9d18b510914feea0cd6b2df7571cb9
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07939546B2

Reaction notes

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