3-Fluoropyrrolidine → HCID 56849220, compound

HRID 1907303Notes

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][C:34]4[CH:38]=[C:37]([CH3:39])[O:36][N:35]=4)([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:40][C@@H:41]1[CH2:45][CH2:44][NH:43][CH2:42]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][C:34]5[CH:38]=[C:37]([CH3:39])[O:36][N:35]=5)([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:43]3[CH2:44][CH2:45][C@@H:41]([F:40])[CH2:42]3)=[CH:3][CH:4]=2)(=[O:10])=[O:9])[CH2:20][CH2:19]4)=[CH:25][CH:26]=1

Participants

Reactant 2

HCID 27591633-Fluoropyrrolidine

HCID 86669990HCID 86669990, compound

Product 1

HCID 56849220HCID 56849220, compound

Procedure

The title compound was prepared by the method of Example 20 using (R)-6-(6-chloropyridine-3-sulfonyl)-1-(4-fluorophenyl)-4a-(5-methyl-isoxazol-3-ylmethoxymethyl)-4,4a,5,6,7,8-hexahydro-1H-1,2,6-triaza-cyclopenta[b]naphthalene and (R)-3-fluoropyrrolidine. 1H NMR (400 MHz, CHCl3-d): δ 8.55 (d, 1H), 7.77 (dd, 1H), 7.49-7.37 (m, 3H), 7.14 (t, 2H), 6.41 (d, 1H), 6.35-6.20 (m, 2H), 5.40 (d, 1H), 4.62-4.48 (m, 2H), 4.19 (dd, 1H), 3.78-3.70 (m, 3H), 3.51 (d, 1H), 3.18-3.10 (m, 2H), 2.69-2.60 (m, 1H), 2.42 (d, 3H), 2.21 (d, 1H), 2.10 (d, 1H).

Sources & evidence

ORD record: ord-4a8b6c04de32465db7e3af5a8abdcf5e
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598154B2

Reaction notes

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