Diisopropylethylamine → HCID 11965613, compound

HRID 906554Notes

Reaction equation

[CH3:1][S:2]([NH:5][NH2:6])(=[O:4])=[O:3].CCN(C(C)C)C(C)C.C[O:17][C:18](=O)[C:19]1[CH:24]=[C:23]([C:25]2[N:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)[C:22]([C:31]([F:34])([F:33])[F:32])=[CH:21][C:20]=1[NH:35][C:36](OC1C=CC(Cl)=CC=1)=[O:37]>O1CCOCC1>[CH3:30][N:26]1[CH:27]=[CH:28][CH:29]=[C:25]1[C:23]1[CH:24]=[C:19]2[C:20](=[CH:21][C:22]=1[C:31]([F:32])([F:33])[F:34])[NH:35][C:36](=[O:37])[N:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[C:18]2=[O:17]

Participants

Conditions

Temperature: 95 °C

Procedure

CH3SO2NHNH2 (25.5 mg, 1.5 equiv) and i-Pr2NEt (26.5 μL, 1 equiv) were added to a solution of 2-(4-chloro-phenoxycarbonylamino)-5-(1-methyl-1H-pyrrol-2-yl)-4-trifluoromethyl-benzoic acid methyl ester (70 mg, 0.155 mmol) in dioxane (2 mL). The mixture was stirred for 2 h (TLC control) at 95° C. CH3SO2NHNH2 (25.5 mg, 1.5 equiv) and i-Pr2NEt (26.5 μL, 1 equiv) were then added. The mixture was stirred for 48 h at 95° C. The mixture was evaporated to dryness. The crude product was purified by column chromatography (silica gel 60, EtOAc/hexanes 7/3) to give N-[6-(1-methyl-1H-pyrrol-2-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide (50 mg, 80%) as a yellow solid. ESI-MS: m/z 420 [M+NH4]+, rt: 4.83 min. 1H-NMR (DMSO-d6, 400 MHz) 7.91 (s, 2H), 7.57 (s, 1H), 7.54 (s, 1H), 3.88 (s, 3H), 3.14 (s, 3H).

Workup

stirringThe mixture was stirred for 48 h at 95° C
customThe mixture was evaporated to dryness
customThe crude product was purified by column chromatography (silica gel 60, EtOAc/hexanes 7/3)

Sources & evidence

ORD record: ord-392ddb23437b4200980b5cfc72168e43
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012988B2

Reaction notes

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