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Lithium iodide → (S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-oxo-2,6-naphthyridin-2(1H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid

HRID 879365
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HRID 879365 반응식
[C:1]([O:5][C@@H:6]([C:12]1[C:37]([CH3:38])=[CH:36][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[N:30][CH:31]=5)[C:26]4=[O:35])[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)[C:7]([O:9]CC)=[O:8])([CH3:4])([CH3:3])[CH3:2].[Li+].[I-]>N1C=CC=CC=1>[C:1]([O:5][C@@H:6]([C:12]1[C:37]([CH3:38])=[CH:36][C:15]2[N:16]=[C:17]([C:19]3[CH:24]=[CH:23][N:22]=[C:21]([N:25]4[CH:34]=[CH:33][C:32]5[C:27](=[CH:28][CH:29]=[N:30][CH:31]=5)[C:26]4=[O:35])[CH:20]=3)[S:18][C:14]=2[C:13]=1[C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]
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4

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HCID 66321Lithium iodideHCID 86700170(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-oxo-2,6-naphthyridin-2(1H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate

생성물 1

HCID 86700171(S)-2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-oxo-2,6-naphthyridin-2(1H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetic acid

시약·촉매·용매 1

HCID 1049Pyridine용매

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온도
170 °C

실험 절차

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(1-oxo-2,6-naphthyridin-2(1H)-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (15.5 mg, 0.024 mmol) in pyridine (0.8 mL) was added LiI (100 mg, excess). The reaction mixture was heating in a microwave at 170° C. for 90 min. The mixture was concentrated in vacuo and then purified by reverse phase HPLC, eluting by 0-100% acetonitrile in H2O with 0.1% TFA to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C33H28ClN4O4S: 611.2; found: 611.2. 1H NMR (400 MHz, CDCl3) δ 9.32 (s, 1H), 8.81 (d, J=6.0 Hz, 1H), 8.75-8.71 (m, 2H), 8.60 (s, 1H), 8.27 (d, J=7.6 Hz, 1H), 7.99 (d, J=3.6 Hz, 1H), 7.94 (s, 1H), 7.70 (d, J=8.0 Hz, 1H), 7.53-7.48 (m, 3H), 6.94 (d, J=8.0 Hz, 1H), 5.32 (s, 1H), 2.59 (s, 3H), 1.00 (s, 9H).

후처리

  1. concentrationThe mixture was concentrated in vacuo
  2. custompurified by reverse phase HPLC
  3. washeluting by 0-100% acetonitrile in H2O with 0.1% TFA

출처 및 근거

ORD 기록
ord-63f147cd0afe46bcadd638fa38efc12d
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08987250B2

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