Diisopropylethylamine → HCID 11965536, compound

HRID 906543Notes

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-45a8e42053964403acdf4b28b32a01d6
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012988B2

Reaction notes

Loading…