5-Bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)nicotinamide → N-(4-(Chlorodifluoromethoxy)phenyl)-5-(5-cyano-1H-pyrrol-2-yl)-6-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)nicotinamide

HRID 525710ノート

反応式

HRID 525710 の反応式
Br[C:2]1[C:3]([N:22]2[CH2:26][C@H:25]([OH:27])[C@@H:24]([OH:28])[CH2:23]2)=[N:4][CH:5]=[C:6]([CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:17]([Cl:20])([F:19])[F:18])=[CH:12][CH:11]=1)=[O:8].C(OC([N:36]1[C:40]([C:41]#[N:42])=[CH:39][CH:38]=[C:37]1B(O)O)=O)(C)(C)C>>[Cl:20][C:17]([F:19])([F:18])[O:16][C:13]1[CH:14]=[CH:15][C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:21]=[C:2]([C:37]3[NH:36][C:40]([C:41]#[N:42])=[CH:39][CH:38]=3)[C:3]([N:22]3[CH2:26][C@H:25]([OH:27])[C@@H:24]([OH:28])[CH2:23]3)=[N:4][CH:5]=2)=[CH:11][CH:12]=1

参加物

3

反応物 2

HCID 899065275-Bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)nicotinamideHCID 89907888(1-(tert-butoxycarbonyl)-5-cyano-1H-pyrrol-2-yl)boronic acid

生成物 1

HCID 118044938N-(4-(Chlorodifluoromethoxy)phenyl)-5-(5-cyano-1H-pyrrol-2-yl)-6-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)nicotinamide

実験手順

The title compound was prepared in an analogous fashion to that described in Example 29 using 5-bromo-N-(4-(chlorodifluoromethoxy)phenyl)-6-((3S,4S)-3,4-dihydroxypyrrolidin-1-yl)nicotinamide (Stage 46.1) and (1-(tert-butoxycarbonyl)-5-cyano-1H-pyrrol-2-yl)boronic acid (Stage 29.1) to afford a rose solid. UPLC-MS (Condition 3) tR=0.97 min, m/z=490.0 [M+H]+, m/z=487.9 [M−H]−; 1H NMR (400 MHz, DMSO-d6) δ ppm 3.02 (d, J=11.86 Hz, 2H) 3.46 (dd, J=11.86, 3.55 Hz, 2H) 3.90 (br. s, 2H) 5.09 (d, J=2.93 Hz, 2H) 6.29 (dd, J=3.67, 2.45 Hz, 1H) 7.03 (dd, J=3.67, 2.32 Hz, 1H) 7.34 (d, J=9.17 Hz, 2H) 7.83-7.90 (m, 2H) 8.07 (d, J=2.32 Hz, 1H) 8.76 (d, J=2.32 Hz, 1H) 10.18 (s, 1H) 12.63-12.68 (m, 1H).

後処理

  1. customto afford a rose solid

出典と根拠

ORDレコード
ord-97b294f3a8b04ca098c932a14dbd3f70
出典データセット
uspto-grants-2016_05
特許番号
US09340537B2

反応ノート

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