(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide → HCID 67009450, compound

HRID 1630205Notes

Reaction equation

HRID 1630205 reaction equation
Cl.[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]([OH:14])=O)=[CH:3]1.[CH2:15]([C@H:22]1[CH2:26][NH:25][C@H:24]([C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[CH:32][CH:31]=2)=[O:28])[CH2:23]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]([N:25]2[CH2:26][C@H:22]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH2:23][C@H:24]2[C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([O:36][C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[CH:32][CH:31]=2)=[O:28])=[O:14])=[CH:3]1

Participants

3

Reactant 2

HCID 67009148(2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamideHCID 67010489HCID 67010489, compound

Product 1

HCID 67009450HCID 67009450, compoundYield 39.3%

Procedure

Proceeding as in Example 1, but substituting 2-(1H-indol-3-yl)acetic acid hydrochloride and (2S,4R)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide, gave Compound 98, (2S,4R)-1-(2-(1H-indol-3-yl)acetyl)-4-benzyl-N-(4-(4-fluorophenoxy)phenyl)pyrrolidine-2-carboxamide (12.9 mg, 39.3%). Major isomer: 1H-NMR (400 MHz, DMSO-D6): σ 10.91 (s, 1H), 9.99 (s, 1H), 7.56 (m, 3H), 7.35-7.07 (m, 10H), 7.01-6.94 (m, 5H), 4.50 (m, 1H), 3.75 (m, 2H), 3.69 (s, 2H), 2.61 (m, 3H), 1.90 (m, 2H). MS (EI) for C34H30FN3O3. found 548.6 (MH+).

Sources & evidence

ORD record
ord-430b120de6e8400ea04bd464ac8888b7
Source dataset
uspto-grants-2014_07
Patent number
US08791102B2

Reaction notes

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