Diisopropylethylamine → HCID 11965536, compound

HRID 1894047Notes

Reaction equation

C[O:2][C:3](=O)[C:4]1[CH:9]=[C:8]([C:10]2[N:11]=[N:12][N:13]([CH3:15])[CH:14]=2)[C:7]([C:16]([F:19])([F:18])[F:17])=[CH:6][C:5]=1[NH:20][C:21]([O:23]C1C=CC(Cl)=CC=1)=O.CCN(C(C)C)C(C)C.[CH3:41][S:42]([NH:45][NH2:46])(=[O:44])=[O:43]>O1CCOCC1>[CH3:15][N:13]1[CH:14]=[C:10]([C:8]2[CH:9]=[C:4]3[C:5](=[CH:6][C:7]=2[C:16]([F:19])([F:18])[F:17])[NH:20][C:21](=[O:23])[N:46]([NH:45][S:42]([CH3:41])(=[O:44])=[O:43])[C:3]3=[O:2])[N:11]=[N:12]1

Participants

Conditions

Temperature: 100 °C

Procedure

2-(4-Chloro-phenoxycarbonylamino)-5-(1-methyl-1H-[1,2,3]triazol-4-yl)-4-trifluoromethyl-benzoic acid methyl ester (260 mg, 0.57 mmol) was dissolved in dioxane (15 mL). After addition of i-Pr2NEt (294 μL, 3 equiv) and CH3SO2NHNH2 (126 mg, 2 equiv), the solution was stirred for 2 h at 100° C. The solvent was removed in vacuo and the crude product was dried in vacuo for 2 h. DCM (5 mL) was then added and, after sonication, the solution was put in the freezer for 16 h. The resulting solid was filtered off, washed with DCM and dried to afford N-[6-(1-methyl-1H-[1,2,3]triazol-4-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide (180 mg, 78%) as an off-white solid. (ESI-MS: m/z 446.5 [M+CH3CN+H]+, rt 3.71 min) 1H-NMR (DMSO-d6, 400 MHz) 8.33 (s, 1H), 8.28 (s, 1H), 7.64 (s, 1H), 4.13 (s, 3H), 3.16 (s, 3H).

Workup

customThe solvent was removed in vacuo
dry with materialthe crude product was dried in vacuo for 2 h
additionDCM (5 mL) was then added
customafter sonication
waitthe solution was put in the freezer for 16 h
filtrationThe resulting solid was filtered off
washwashed with DCM
customdried

Sources & evidence

ORD record: ord-aadf9fc10c0241da9e1422e908dc90c9
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08513268B2

Reaction notes

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