2-(Dimethylamino)ethanol → HCID 59632616, compound

HRID 2369101Notes

Reaction equation

[CH3:1][S:2]([C:5]1[CH:6]=[C:7]([C:11]2[S:15][C:14]([C:16]3[N:20]([C:21]4[CH:22]=[C:23]([OH:27])[CH:24]=[CH:25][CH:26]=4)[N:19]=[C:18]([C:28]([F:31])([F:30])[F:29])[CH:17]=3)=[CH:13][CH:12]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:4])=[O:3].[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1.C(Cl)Cl>[CH3:32][N:33]([CH3:37])[CH2:34][CH2:35][O:27][C:23]1[CH:24]=[CH:25][CH:26]=[C:21]([N:20]2[C:16]([C:14]3[S:15][C:11]([C:7]4[CH:8]=[CH:9][CH:10]=[C:5]([S:2]([CH3:1])(=[O:4])=[O:3])[CH:6]=4)=[CH:12][CH:13]=3)=[CH:17][C:18]([C:28]([F:31])([F:29])[F:30])=[N:19]2)[CH:22]=1

Participants

Conditions

Temperature: 0 °C

Procedure

3-(5-(5-(3-(methylsulfonyl)phenyl)thiophen-2-yl)-3-(trifluoromethyl)-1H-pyrazol-1-yl)phenol (120 mg, 0.26 mmol), 2-(dimethylamino)ethanol (46 mg, 0.52 mmol) and triphenylphosphine (138 mg, 0.52 mmol) were dissolved in a mixture solvent of anhydrous THF (2.5 mL) and DCM (2.5 mL) and cooled off at 0° C. under nitrogen atmosphere. To this solution was added diisopropyl azodicarboxylate (111 mg, 0.52 mmol). The reaction mixture was stirred vigorously and warmed up to mom temperature overnight. The solvent was evaporated in vacuo and the residue was purified by HPLC, providing the product (61 mg, 44%). 1H-NMR (Acetone-d6): δ 8.13 (m, 1H), 7.93 (m, 1H), 7.90 (m, 1H), 7.71 (m, 1H), 7.60 (m, 1H), 7.47 (m, 1H), 7.17-7.09 (br, 5H), 4.12 (t, J=5.8 Hz, 2H), 3.18 (s, 3H), 2.65 (t, J=5.8 Hz, 2H), 2.21 (s, 6H). MS (ES): 536 [M+H]+.

Workup

temperaturewarmed up to mom temperature overnight
customThe solvent was evaporated in vacuo
customthe residue was purified by HPLC

Sources & evidence

ORD record: ord-6173554ef2864556af57d3b7abb66c47
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08703805B2

Reaction notes

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