p-Toluenesulfonic acid → HCID 71577667, compound

HRID 2401478Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=1.[NH2:14][C:15]1[C:27]([Cl:28])=[CH:26][C:18]2[C:19](=[O:25])[N:20]([CH3:24])[CH2:21][CH2:22][O:23][C:17]=2[CH:16]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[Cl:28][C:27]1[C:15]([NH:14][C:2]2[N:7]=[C:6]([NH:8][CH3:9])[C:5]([C:10]([F:13])([F:12])[F:11])=[CH:4][N:3]=2)=[CH:16][C:17]2[O:23][CH2:22][CH2:21][N:20]([CH3:24])[C:19](=[O:25])[C:18]=2[CH:26]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-chloro-N-methyl-5-(trifluoromethyl)pyrimidin-4-amine (0.5 g, 2.36 mmol), 8-amino-7-chloro-4-methyl-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one (0.38 mmol) and p-toluene sulphonic acid (0.49 g, 2.6 mmol) in dioxane (10 mL) was heated at 100° C. for 2 h. The mixture was cooled, filtered and the solid washed with dioxane. The solid was dried in a vacuum oven and purified via silica gel column chromatography (20-100% ethyl acetate/isohexane) gave 7-chloro-4-methyl-8-(4-(methylamino)-5-(trifluoromethyl)pyrimidin-2-ylamino)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one as a white solid (10 mg, 28%). LCMS (10 cm_ESCI_Formic_MeCN): [MH+]=402 at 3.04 min. 1H NMR δ (ppm)(400 MHz, CDCl3): 8.41 (1H, s), 8.22 (1H, s), 7.97 (1H, s), 7.77-7.67 (1H, m), 5.29 (1H, s), 4.47-4.39 (2H, m), 3.61-3.51 (2H, m), 3.21-3.18 (3H, m), 3.20-3.07 (3H, m).

Workup

temperatureThe mixture was cooled
filtrationfiltered
washthe solid washed with dioxane
customThe solid was dried in a vacuum oven
custompurified via silica gel column chromatography (20-100% ethyl acetate/isohexane)

Sources & evidence

ORD record: ord-a854acf7775d4fd7ab031c9e5070e539
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796296B2

Reaction notes

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