(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67010437, compound

HRID 1630206Notes

Reaction equation

HRID 1630206 reaction equation
Cl.[O:2]=[C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[CH:4]1[CH2:13][C:14]([OH:16])=O.[CH2:17]([C@H:24]1[CH2:28][NH:27][C@H:26]([C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][C:39]3[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=3)=[CH:34][CH:33]=2)=[O:30])[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[CH2:17]([C@H:24]1[CH2:28][N:27]([C:14](=[O:16])[CH2:13][CH:4]2[C:5](=[O:12])[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]2=[O:2])[C@H:26]([C:29]([NH:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][C:39]3[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=3)=[CH:34][CH:33]=2)=[O:30])[CH2:25]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67009354HCID 67009354, compound

Product 1

HCID 67010437HCID 67010437, compoundYield 40.1%

Procedure

Proceeding as in Example 1, but substituting 2-(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 97, (2S,4R)-4-benzyl-1-(2-(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl)-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (13.9 mg, 40.1%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 9.94 (s, 1H), 7.86 (m, 4H), 7.51 (d, 2H), 7.31-7.13 (m, 9H), 6.91 (m, 2H), 4.52 (d, 1H), 4.47-4.40 (m, 2H), 3.84 (m, 1H), 3.39 (m, 1H), 2.67 (m, 3H), 1.94 (m, 2H). MS (EI) for C34H28FN3O5. found 578.6 (MH+).

Sources & evidence

ORD record
ord-ecabefd09296409c87171238e7b9e1e3
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

Loading…