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Trifluoroacetic acid → 1-[5-(4-Methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}pyridin-2-yl)-1,3-thiazol-2-yl]-1-(pyrrolidin-3-yl)ethanol

HRID 2272676
ノート
印刷プレビュー

反応式

HRID 2272676 の反応式
FC(F)(F)C(O)=O.[OH:8][C:9]([CH:34]1[CH2:38][CH2:37][N:36](C(OC(C)(C)C)=O)[CH2:35]1)([C:11]1[S:12][C:13]([C:16]2[CH:21]=[C:20]([CH3:22])[CH:19]=[C:18]([NH:23][C:24]3[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][N:25]=3)[N:17]=2)=[CH:14][N:15]=1)[CH3:10]>ClCCl>[CH3:22][C:20]1[CH:19]=[C:18]([NH:23][C:24]2[CH:29]=[C:28]([C:30]([F:33])([F:31])[F:32])[CH:27]=[CH:26][N:25]=2)[N:17]=[C:16]([C:13]2[S:12][C:11]([C:9]([CH:34]3[CH2:38][CH2:37][NH:36][CH2:35]3)([OH:8])[CH3:10])=[N:15][CH:14]=2)[CH:21]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 86715346Tert-butyl 3-{1-hydroxy-1-[5-(4-methyl-6-{[4-(trifluoromethyl)-pyridin-2-yl]amino}pyridin-2-yl)-1,3-thiazol-2-yl]ethyl}pyrrolidine-1-carboxylate

生成物 1

HCID 710036931-[5-(4-Methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}pyridin-2-yl)-1,3-thiazol-2-yl]-1-(pyrrolidin-3-yl)ethanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Trifluoroacetic acid (0.4 mL, 5.19 mmol) was added to a solution of tert-butyl 3-{1-hydroxy-1-[5-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}pyridin-2-yl)-1,3-thiazol-2-yl]ethyl}pyrrolidine-1-carboxylate (100 mg, 0.182 mmol) in dichloromethane (0.8 mL). The mixture was stirred at room temperature for 16 hours then concentrated under reduced pressure. The residue was purified on reverse phase HPLC (Sunfire prep C18 OBD 5 uM, acetonitrile/water+0.1% TFA) to afford 1-[5-(4-methyl-6-{[4-(trifluoromethyl)pyridin-2-yl]amino}pyridin-2-yl)-1,3-thiazol-2-yl]-1-(pyrrolidin-3-yl)ethanol as a 1:1 mix of diastereomers. MS ESI calc'd. for C21H22F3N5OS [M+H]+ 450. found 450. 1H NMR (500 MHz, CD3OD) δ 8.55 (d, J=5.6 Hz, 1H), 8.37 (d, 11-1, two singlets from two diastereomers), 8.12 (s, 1H), 7.46 (s, 1H), 7.37 (d, J=5.5 Hz, 1H), 7.05 (s, 1H), 3.58-2.95 (m, 5H, two sets of peaks from two diastereomers), 2.45 (s, 3H), 2.30-1.79 (m, 2H, two sets of peaks from two diastereomers), 1.69 (d, 3H, two singlets from two diastereomers). rhSyk activity=+++.

後処理

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was purified on reverse phase HPLC (Sunfire prep C18 OBD 5 uM, acetonitrile/water+0.1% TFA)

出典と根拠

ORDレコード
ord-321cf60f3c61402d96048200b6ea7924
出典データセット
uspto-grants-2015_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09120785B2

反応ノート

読み込み中…

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