Diisopropylethylamine → HCID 2842558, compound

HRID 540770Notes

Reaction equation

C(N(C(C)C)CC)(C)C.C(N1C(O[C:18]2[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][CH:19]=2)=CC(C2C=CC=C(C(NS(CC(F)(F)F)(=O)=O)(C)C)C=2)=N1)C.[O:45]1[CH2:49][CH2:48][CH2:47][CH:46]1[CH2:50][NH2:51]>CN(C=O)C>[O:45]1[CH2:49][CH2:48][CH2:47][CH:46]1[CH2:50][NH:51][C:22](=[O:23])[C:21]1[CH:25]=[CH:26][CH:18]=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 22 °C

Procedure

(1-benzotriazol-1-yloxy)[tris(dimethylamino)]phosphonium hexafluorophosphate (52 mg, 0.12 mmol, 1.2 equiv) and diisopropylethylamine (38 mg, 0.29 mmol, 3 equiv) were added to a stirring solution of 4-({1-ethyl-3-[3-(2-{[(2,2,2-trifluoroethyl)sulfonyl]amino}propan-2-yl)phenyl]-1H-pyrazol-5-yl}oxy)benzoic acid (50 mg, 0.10 mmol, 1 equiv) in DMF (1 mL). 1-(tetrahydrofuran-2-yl)methanamine (20 mg, 0.20 mmol, 2 equiv) was then added and the mixture was stirred at 22° C. for 16 hours. The mixture was purified directly by reversed phase HPLC (0-95% acetonitrile:water with 0.025% TFA). Pure fractions were identified, combined, and lyophilized to give 4-({1-ethyl-3-[3-(2-{[(2,2,2-trifluoroethyl)sulfonyl]amino}propan-2-yl)phenyl]-1H phenyl]-1H-pyrazol-5-yl}oxy)-N-(tetrahydrofuran-2-ylmethyl)benzamide (38% yield). Calc'd (M+1)+: 595.2. Found: 595.1

Workup

customThe mixture was purified directly by reversed phase HPLC (0-95% acetonitrile:water with 0.025% TFA)

Sources & evidence

ORD record: ord-c5961a376e3e4e389ca3b8997943eccd
Source dataset: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08871796B2

Reaction notes

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