Sulfamide → 4-(4-{3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-pyrazol-1-yl)-piperidine-1-sulfonic acid amide

HRID 2046928Notes

Reaction equation

[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]4)[CH:25]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11].[S:32](N)([NH2:35])(=[O:34])=[O:33]>O1CCOCC1>[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[CH:10]([C:12]1[C:20]2[C:15](=[N:16][CH:17]=[C:18]([C:21]3[CH:22]=[N:23][N:24]([CH:26]4[CH2:27][CH2:28][N:29]([S:32]([NH2:35])(=[O:34])=[O:33])[CH2:30][CH2:31]4)[CH:25]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11]

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine (8.0 mg, 0.0174 mmol), sulfamide (3.35 mg, 0.0349 mmol) and dioxane (2 mL) was heated to 90° C. overnight in a sealed tube. The solution was concentrated in vacuo, redissolved in MeOH and purified via HPLC. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.89 (d, J=7.1 Hz, 3 H), 2.09-2.25 (m, 4 H), 2.76-2.91 (m, 2H), 3.78 (d, J=12.4 Hz, 2 H), 4.30 (dt, J=10.4, 5.3 Hz, 1 H), 5.29 (q, J=7.4 Hz, 1 H), 7.15-7.23 (m, 1 H), 7.36 (d, J=1.5 Hz, 1 H), 7.38-7.53 (m, 2 H), 7.58 (s, 1 H), 7.92 (s, 1 H), 8.32 (d, J=1.8 Hz, 1 H). MS (ES+): m/z 537.02 (100) [MH+]. HPLC: tR=3.36 min (ZQ3, polar—5 min).

Workup

concentrationThe solution was concentrated in vacuo
dissolutionredissolved in MeOH
custompurified via HPLC
additionThe fractions containing the pure product
concentrationwere concentrated in vacuo

Sources & evidence

ORD record: ord-452a7b96ce444a7e86095266981f81db
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592448B2

Reaction notes

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