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

HRID 2046925Notes

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[CH2:22][CH2:23][NH:24][CH2:25][CH:26]=3)[CH:19]=2)[NH:14][CH:13]=1)[CH3:11].[S:27](N)([NH2:30])(=[O:29])=[O:28]>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[CH2:22][CH2:23][N:24]([S:27]([NH2:30])(=[O:29])=[O:28])[CH2:25][CH:26]=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-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrrolo[2,3-b]pyridine (10.0 mg, 0.0256 mmol), sulfamide (4.92 mg, 0.0512 mmol) and dioxane (2 mL) was heated to 90° C. for 16 h 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=1.87 (d, J=7.1 Hz, 3 H), 2.40-2.60 (m, 2 H), 3.32-3.35 (m, 2 H), 3.77 (q, J=2.6 Hz, 2 H), 5.26 (q, J=7.1 Hz, 1 H), 5.90-5.96 (m, 1 H), 7.19 (t, J=8.6 Hz, 1 H), 7.29 (s, 1 H), 7.37 (d, J=1.5 Hz, 1 H), 7.42 (br. s., 1 H), 8.28 (br. s., 1 H). MS (ES+): m/z 469.00 (100) [MH+]. HPLC: tR=3.42 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-68426c81c1d544b79b9b7e1209532f6a
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08592448B2

Reaction notes

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