HCID 16065393, compound → HCID 16065531, compound

HRID 2425521Notes

Reaction equation

CS(CC1C(C2C=CC=CC=2)=NC2C(C=1C(N[C@H](C1C=CC=CC=1)CC)=O)=CC=CC=2)=[O:3].[CH:33]([S:36][CH2:37][C:38]1[C:39]([C:60]2[CH:65]=[CH:64][CH:63]=[CH:62][CH:61]=2)=[N:40][C:41]2[C:46]([C:47]=1[C:48]([NH:50][C@H:51]([C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)[CH2:52][CH3:53])=[O:49])=[CH:45][CH:44]=[CH:43][CH:42]=2)([CH3:35])[CH3:34]>>[CH:33]([S:36]([CH2:37][C:38]1[C:39]([C:60]2[CH:61]=[CH:62][CH:63]=[CH:64][CH:65]=2)=[N:40][C:41]2[C:46]([C:47]=1[C:48]([NH:50][C@H:51]([C:54]1[CH:55]=[CH:56][CH:57]=[CH:58][CH:59]=1)[CH2:52][CH3:53])=[O:49])=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:3])([CH3:34])[CH3:35]

Participants

Reactant 2

HCID 16065393HCID 16065393, compound

HCID 16065395HCID 16065395, compound

Product 1

HCID 16065531HCID 16065531, compound

Procedure

This compound [two diastereomers] was prepared similarly to 3-[(methylsulfinyl)methyl]-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (2, scheme 1) except 3-[(isopropylthio)methyl]-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (Example 13) was used instead of 3-[(methylthio)methyl]-2-phenyl-N-[(1S)-1-phenylpropyl]quinoline-4-carboxamide (1). 1H NMR (300 MHz, CDCl3) δ 8.90-8.68 (m, 1H), 8.16-8.03 (m, 2H), 7.80-7.27 (m, 12H), 5.35-5.12 (m, 1H), 4.30-3.67 (m, 2H), 2.86-1.83 (m, 3H), 1.19-0.55 (m, 9H); HRMS m/z 471.2077, calcd 471.2106.

Sources & evidence

ORD record: ord-e7d0434b38124772afc7d448785b5f7d
Source dataset: uspto-grants-2011_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07964733B2

Reaction notes

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