(2S)-2β,5α-Dimethylpyrrolidine → HCID 131723846, compound

HRID 1264977Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[C:4]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([CH2:19][C@H:20]([NH:26][C:27]3[C:30](=O)[C:29](=[O:32])[C:28]=3[O:33]C(C)C)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15][CH:14]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[N:7][CH:6]=2.[CH3:37][C@H:38]1[CH2:42][CH2:41][C@@H:40]([CH3:43])[NH:39]1>>[CH3:1][C:2]1[N:3]=[C:4]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][C@H:20]([NH:26][C:27]3[C:28](=[O:33])[C:29](=[O:32])[C:30]=3[N:39]3[C@H:40]([CH3:43])[CH2:41][CH2:42][C@@H:38]3[CH3:37])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:17][CH:18]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[N:7][CH:6]=2

Participants

Reactant 2

HCID 5324511(2S)-2β,5α-Dimethylpyrrolidine

HCID 91509257Ethyl (s)-3-[4-(3-methyl-2,7-naphthyridin-1-ylamino)phenyl]-2-[2-isopropoxy-3,4-dioxocyclobut-1-enylamino]propanoate

Product 1

HCID 131723846HCID 131723846, compound

Procedure

Prepared in a similar manner to the compound of Example 33, from the compound of Example 30 and cis 2,5-dimethylpyrrolidine. δH (DMSO-d6), 9.75 (1H, s), 9.45 (1H, s), 8.56 (1H, d, J 5.6 Hz), 7.84 (2H, m), 7.65 (1H, d, J 9.1 Hz), 7.55 (1H, d, J 5.6 Hz), 7.23 (2H, d, J 8.5 Hz), 6.96 (1H, s), 5.13 (1H, m), 4.22-4.13 (4H, m), 3.22 (1H, dd, J 13.9, 4.6 Hz), 3.04 (1H, dd, J 13.8, 10.6 (Hz), 2.43 (3H, s), 2.12-2.05 (2H, m), 1.70-1.64 (2H, m), 1.24-1.15 (9H, m); m/z (ES+, 70V) 528 (MH+).

Sources & evidence

ORD record: ord-a29a8dfbab374f8a88bd6c1b9d56ae4b
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545013B2

Reaction notes

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