Diethylcarbamoyl chloride → HCID 178464307, compound

HRID 2274397Notes

Reaction equation

[F:1][C:2]1[C:22]([O:23][CH2:24][CH2:25][CH2:26][N:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)=[CH:21][C:5]2[NH:6][C:7]([C:9]3[C:13]([NH2:14])=[CH:12][N:11]([CH:15]4[CH2:20][CH2:19][CH2:18][CH2:17][O:16]4)[N:10]=3)=[N:8][C:4]=2[CH:3]=1.[CH2:33]([N:35]([CH2:39][CH3:40])[C:36](Cl)=[O:37])[CH3:34].C(N(CC)C(C)C)(C)C>O1CCCC1>[CH2:33]([N:35]([CH2:39][CH3:40])[C:36]([NH:14][C:13]1[C:9]([C:7]2[NH:6][C:5]3[CH:21]=[C:22]([O:23][CH2:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]4)[C:2]([F:1])=[CH:3][C:4]=3[N:8]=2)=[N:10][N:11]([CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][O:16]2)[CH:12]=1)=[O:37])[CH3:34]

Participants

Conditions

Temperature: 50 °C

Procedure

130 mg of 3-[5-fluoro-6-(3-piperidin-1-ylpropoxy)-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-ylamine are solubilized in 10 mL of tetrahydrofuran and then 372 μl of diethylcarbamoyl chloride and 487 μL of N,N-diisopropylethylamine are added. The reaction medium is heated at 50° C. over night. The solvent is evaporated off under vacuum in a rotary evaporator and the reaction crude is purified by flash chromatography on a 4 g silica cartridge, eluent: 100/0 to 80/20 dichloromethane/methanol. 70 mg of 1,1-diethyl-3-[3-[5-fluoro-6-(3-piperidin-1-ylpropoxy)-1H-benzimidazol-2-yl]-1-(tetrahydropyran-2-yl)-1H-pyrazol-4-yl]urea are isolated in the form of a chestnut-brown oil. Analytical LC/MS: Tr=2.91 min, [M+H]+=542.00 DAD=95%.

Workup

customThe solvent is evaporated off under vacuum in a rotary evaporator
customthe reaction crude
customis purified by flash chromatography on a 4 g silica cartridge, eluent

Sources & evidence

ORD record: ord-5e9ce090911d4c78b8d2a3e653047678
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09126969B2

Reaction notes

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