Potassium Carbonate → HCID 178449967, compound

HRID 1484985Notes

Reaction equation

FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([CH:13]2[CH2:15][CH2:14]2)[N:10]=[C:9]([C:16]2[S:17][C:18]([S:21](=[O:28])(=[O:27])[NH:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:19][CH:20]=2)[N:8]=1)(=O)=O.[NH2:31][C:32]1[N:36](C(OC(C)(C)C)=O)[N:35]=[C:34]([CH:44]2[CH2:46][CH2:45]2)[CH:33]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[C:23]([NH:22][S:21]([C:18]1[S:17][C:16]([C:9]2[N:10]=[C:11]([CH:13]3[CH2:15][CH2:14]3)[CH:12]=[C:7]([NH:31][C:32]3[NH:36][N:35]=[C:34]([CH:44]4[CH2:46][CH2:45]4)[CH:33]=3)[N:8]=2)=[CH:20][CH:19]=1)(=[O:27])=[O:28])([CH3:26])([CH3:25])[CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of crude 2-(5-(N-tert-butylsulfamoyl)thiophen-2-yl)-6 cyclopropylpyrimidin-4-yl trifluoromethanesulfonate 220 mg, 0.41 mmol, 1.0 equiv.), tert-butyl 5-amino-3-cyclopropyl-1H-pyrazole-1-carboxylate (138 mg, 0.62 mmol, 1.2 equiv.), Ph3P (33 mg, 0.12 mmol, 0.3 equiv.), Ph(Ph3P)4 (47 mg, 0.041 mmol, 0.1 equiv.) and K2CO3 (170 mg, 1.23 mmol, 3 equiv.) in dioxane (5 mL) was stirred at 100° C. for 3 h. The mixture was extracted with EtOAc. The combined organic phase was washed (brine), dried (Na2SO4), filtered and concentrated to give a residue, which was purified by silica gel column chromatography (PE/EtOAc/MeOH=1:1:0.1) to provide N-tert-butyl-5-(4-cyclopropyl-6-(3-cyclopropyl-1H-pyrazol-5-ylamino)pyrimidin-2-yl)thiophene-2-sulfonamide (50 mg, 27%) as a white solid. LC-MS (m/z)=459.1 [M+H]+

Workup

extractionThe mixture was extracted with EtOAc
washThe combined organic phase was washed (brine)
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated
customto give a residue, which
customwas purified by silica gel column chromatography (PE/EtOAc/MeOH=1:1:0.1)

Sources & evidence

ORD record: ord-ea5795e3864843279e768c359c55396a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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