Sulfamide → 4-{6-Amino-7-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-3,6-dihydropyridine-1(2H)-sulfonamide

HRID 911967Notes

Reaction equation

HRID 911967 reaction equation
[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[C@H:10]([O:12][C:13]1[C:14]2[O:22][CH:21]=[C:20]([C:23]3[CH2:24][CH2:25][NH:26][CH2:27][CH:28]=3)[C:15]=2[CH:16]=[N:17][C:18]=1[NH2:19])[CH3:11].[S:29](N)([NH2:32])(=[O:31])=[O:30]>O1CCOCC1>[NH2:19][C:18]1[N:17]=[CH:16][C:15]2[C:20]([C:23]3[CH2:24][CH2:25][N:26]([S:29]([NH2:32])(=[O:31])=[O:30])[CH2:27][CH:28]=3)=[CH:21][O:22][C:14]=2[C:13]=1[O:12][C@@H:10]([C:3]1[C:4]([Cl:9])=[CH:5][CH:6]=[C:7]([F:8])[C:2]=1[Cl:1])[CH3:11]

Participants

4

Reactant 2

HCID 82267SulfamideHCID 578124807-[(R)-1-(2,6-Dichloro-3-fluorophenyl)ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)furo[3,2-c]pyridin-6-ylamine

Product 1

HCID 578125514-{6-Amino-7-[(1R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-3-yl}-3,6-dihydropyridine-1(2H)-sulfonamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 7-[(R)-1-(2,6-Dichloro-3-fluorophenyl)-ethoxy]-3-(1,2,3,6-tetrahydropyridin-4-yl)-furo[3,2-c]pyridin-6-ylamine (0.0300 g, 0.071 mmol) and Sulfamide (0.00819 g, 0.0852 mmol) in 1,4-Dioxane (2 mL) was stirred under reflux for 7 h. The reaction mixture was directly loaded onto prep TLC for purification (silica gel, eluting with 4% MeOH in DCM) to afford the title compound as a yellow solid. 1H-NMR (CD3OD, 400 MHz): δ=1.87 (d, J=6.6 Hz, 3H), 2.60 (d, J=1.5 Hz, 2H), 3.36 (t, J=5.7 Hz, 2H), 3.85 (d, J=2.8 Hz, 2H), 6.29 (br. s., 1H), 6.49 (q, 1H), 7.21 (t, J=8.7 Hz, 1H), 7.39 (dd, J=9.0, 4.9 Hz, 1H), 7.64 (s, 1H), 8.19 (s, 1H). MS (ES+): m/z 500.98 (MH+, 35Cl, 37Cl), 502.88 (MH+, 37Cl, 37Cl). HPLC: tR=2.92 min (polar—5 min, ZQ3).

Workup

  1. temperatureunder reflux for 7 h
  2. customThe reaction mixture was directly loaded onto prep TLC for purification (silica gel, eluting with 4% MeOH in DCM)

Sources & evidence

ORD record
ord-b980183b359249c2b629b06bf5cad7b6
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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