3-Fluoropyrrolidine → HCID 56849162, compound

HRID 1907301Notes

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][O:35][CH3:36])([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:37][C@@H:38]1[CH2:42][CH2:41][NH:40][CH2:39]1>>[F:30][C:27]1[CH:26]=[CH:25][C:24]([N:21]2[C:16]3[CH:17]=[C:18]4[C@:13]([CH2:31][O:32][CH2:33][CH2:34][O:35][CH3:36])([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:40]3[CH2:41][CH2:42][C@@H:38]([F:37])[CH2:39]3)=[CH:3][CH:4]=2)(=[O:9])=[O:10])[CH2:20][CH2:19]4)=[CH:29][CH:28]=1

Participants

Reactant 2

HCID 27591633-Fluoropyrrolidine

HCID 86669988HCID 86669988, compound

Product 1

HCID 56849162HCID 56849162, compound

Procedure

The title compound was prepared by the method of Example 20 using (R)-6-(6-chloropyridine-3-sulfonyl)-1-(4-fluorophenyl)-4a-(2-methoxyethoxymethyl)-4,4a,5,6,7,8-hexahydro-1,2,6-triaza-cyclopenta[b]naphthalene and (R)-3-fluoropyrrolidine. 1H NMR (400 MHz, CHCl3-d): δ 8.55-8.44 (m, 1H), 7.50-7.39 (m, 3H), 7.19-7.11 (m, 2H), 6.41 (d, 1H), 6.27 (d, 1H), 5.46 (s, 1H), 5.33 (s, 1H), 4.15 (dd, 1H), 3.87 (dd, 2H), 3.73 (d, 1H), 3.68-3.55 (m, 7H), 3.38 (s, 3H), 3.25 (d, 1H), 3.14 (d, 1H), 2.80-2.69 (m, 1H), 2.39-2.25 (m, 3H), 2.17-2.03 (m, 3H).

Sources & evidence

ORD record: ord-ae60cf11093b4cdc845f09e7616ee050
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598154B2

Reaction notes

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