3-Fluoropyrrolidine → 2-{(R)-1-(4-Fluorophenyl)-6-[6-((R)-3-fluoropyrrolidin-1-yl)-pyridine-3-sulphonyl]-1,4,5,6,7,8-hexahydro-1,2,6-triaza-cyclopenta[b]naphthalene-4a-ylmethoxy}-ethanol

HRID 1907302Notes

Reaction equation

HRID 1907302 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([S:8]([N:11]2[CH2:20][CH2:19][C:18]3[C@:13]([CH2:31][O:32][CH2:33][CH2:34][OH:35])([CH2:14][C:15]4[CH:23]=[N:22][N:21]([C:24]5[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=5)[C:16]=4[CH:17]=3)[CH2:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[F:36][C@@H:37]1[CH2:41][CH2:40][NH:39][CH2:38]1>>[F:30][C:27]1[CH:28]=[CH:29][C:24]([N:21]2[C:16]3[CH:17]=[C:18]4[C@:13]([CH2:31][O:32][CH2:33][CH2:34][OH:35])([CH2:14][C:15]=3[CH:23]=[N:22]2)[CH2:12][N:11]([S:8]([C:5]2[CH:6]=[N:7][C:2]([N:39]3[CH2:40][CH2:41][C@@H:37]([F:36])[CH2:38]3)=[CH:3][CH:4]=2)(=[O:9])=[O:10])[CH2:20][CH2:19]4)=[CH:25][CH:26]=1

Participants

3

Reactant 2

HCID 27591633-FluoropyrrolidineHCID 86669989HCID 86669989, compound

Product 1

HCID 568492192-{(R)-1-(4-Fluorophenyl)-6-[6-((R)-3-fluoropyrrolidin-1-yl)-pyridine-3-sulphonyl]-1,4,5,6,7,8-hexahydro-1,2,6-triaza-cyclopenta[b]naphthalene-4a-ylmethoxy}-ethanol

Procedure

The title compound was prepared by the method of Example 20 using 2-[(R)-6-(6-chloropyridine-3-sulfonyl)-1-(4-fluorophenyl)-1,4,5,6,7,8-hexahydro-1,2,6-triaza-cyclopenta[b]naphthalene-4a-ylmethoxy]-ethanol and (R)-3-fluoropyrrolidine. 1H NMR (400 MHz, CHCl3-d): δ 8.55 (d, 1H), 7.78 (dd, 1H), 7.51-7.40 (m, 3H), 7.15 (t, 2H), 6.41 (d, 1H), 6.28 (s, 1H), 5.40 (d, 1H), 4.26 (d, 1H), 3.91 (s, 2H), 3.74-3.61 (m, 6H), 3.55 (d, 1H), 3.48 (d, 1H), 3.21 (d, 1H), 3.13 (d, 1H), 2.49-2.38 (m, 2H), 2.21 (d, 1H), 2.07 (d, 1H).

Sources & evidence

ORD record
ord-42f0ffbbf04e4c8c86017995816fc77a
Source dataset
uspto-grants-2013_12
Patent number
US08598154B2

Reaction notes

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