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Water → Methyl 1-((3-fluoro-4-(5-(1-(4-hydroxyphenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)-azetidine-3-carboxylate

HRID 1177497
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HRID 1177497 반응식
O.C([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([C:19]3[N:24]=[C:23]4[S:25][C:26]([C:28]5[CH:42]=[CH:41][C:31]([CH2:32][N:33]6[CH2:36][CH:35]([C:37]([O:39][CH3:40])=[O:38])[CH2:34]6)=[CH:30][C:29]=5[F:43])=[N:27][C:22]4=[CH:21][CH:20]=3)[CH2:18][CH2:17]2)=[CH:12][CH:11]=1)C1C=CC=CC=1.C(N(CC)CC)C>C1COCC1.CO.C(Cl)Cl.[Pd]>[F:43][C:29]1[CH:30]=[C:31]([CH2:32][N:33]2[CH2:34][CH:35]([C:37]([O:39][CH3:40])=[O:38])[CH2:36]2)[CH:41]=[CH:42][C:28]=1[C:26]1[S:25][C:23]2[C:22]([N:27]=1)=[CH:21][CH:20]=[C:19]([C:16]1([C:13]3[CH:12]=[CH:11][C:10]([OH:9])=[CH:15][CH:14]=3)[CH2:18][CH2:17]1)[N:24]=2
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 962WaterHCID 8471TriethylamineHCID 67111767Methyl 1-(4-(5-(1-(4-(benzyloxy)phenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate

생성물 1

HCID 67111906Methyl 1-((3-fluoro-4-(5-(1-(4-hydroxyphenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)-azetidine-3-carboxylate

시약·촉매·용매 3

HCID 23938
Palladium
촉매
HCID 6344Dichloromethane용매
HCID 21899815MeOH tetrahydrofuran용매

실험 절차

A slurry of palladium 10% on carbon, 50% water (0.26 g), methyl 1-(4-(5-(1-(4-(benzyloxy)phenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)-3-fluorobenzyl)azetidine-3-carboxylate (0.144 g, 0.25 mmol), triethylamine (0.087 mL, 0.62 mmol) in 4 mL of 3:1 THF/MeOH was stirred rapidly under an atmosphere of hydrogen (balloon) for 36 h. The reaction mixture was diluted with DCM, and filtered through celite and concentrated in vacuo. The resulting solid was adsorbed onto 1.4 g silica gel and purified by silica gel chromatography 0-100% EA/hexanes, to give methyl 1-((3-fluoro-4-(5-(1-(4-hydroxyphenyl)cyclopropyl)thiazolo[5,4-b]pyridine-2-yl)phenyl)methyl)-azetidine-3-carboxylate as a white solid. MS (ESI) m/z: calculated: 489.2; Observed: 490.1 (M++1).

후처리

  1. filtrationfiltered through celite and
  2. concentrationconcentrated in vacuo
  3. custompurified by silica gel chromatography 0-100% EA/hexanes

출처 및 근거

ORD 기록
ord-8ed90314e7bc4f3db3c3c2cc0c7b95ef
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07842685B2

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