Diisopropylethylamine → HCID 11965542, compound

HRID 906552Notes

Reaction equation

HRID 906552 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[CH:26]=[N:27][N:28]([CH3:30])[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:28]1[CH:29]=[C:25]([C:23]2[CH:24]=[C:19]3[C:20](=[CH:21][C:22]=2[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]3=[O:17])[CH:26]=[N:27]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 269268MethanesulfonohydrazideHCID 11965541HCID 11965541, compound

Product 1

HCID 11965542HCID 11965542, compoundYield 42%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

CH3SO2NHNH2 (130 mg, 2.4 equiv) and i-Pr2NEt (169 μL, 2 equiv) were added to a solution of 2-(4-chloro-phenoxycarbonylamino)-5-(1-methyl-1H-pyrazol-4-yl)-4-trifluoromethyl-benzoic acid methyl ester (224 mg, 0.49 mmol) in dioxane (11 mL). The mixture was stirred for 19 h (TLC control) at 90° C. The mixture was evaporated to dryness. The crude product was triturated with hexanes and DCM. The formed precipitate was filtered and washed with hexanes to give N-[6-(1-methyl-1H-pyrazol-4-yl)-2,4-dioxo-7-trifluoromethyl-1,4-dihydro-2H-quinazolin-3-yl]-methanesulfonamide (83 mg, 42%) as a white solid. ESI-MS: m/z 404 [M+H]+, 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

  1. customThe mixture was evaporated to dryness
  2. customThe crude product was triturated with hexanes and DCM
  3. filtrationThe formed precipitate was filtered
  4. washwashed with hexanes

Sources & evidence

ORD record
ord-d31edd58e38641f6b2fb4da6585b5bd4
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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