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Sodium Hydroxide → HCID 136333947, 화합물

HRID 1052211
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HRID 1052211 반응식
Br[C:2]1[S:10][C:9]2[C:8](=[O:11])[NH:7][C:6]([CH:12]3[CH:21]4[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]4)[CH2:15][CH2:14][N:13]3C(OC(C)(C)C)=O)=[N:5][C:4]=2[CH:3]=1.[NH2:29][C:30]1[CH:34]=C(Br)S[C:31]=1[C:36]([NH2:38])=O.C(OC(N1CC2CC1(C(O)=O)C2)=O)(C)(C)C.C([Cl:62])(=O)OCC(C)C.[OH-].[Na+]>CO.O1CCCC1.C(N(CC)CC)C>[ClH:62].[CH:12]1([C:6]2[NH:7][C:8](=[O:11])[C:9]3[S:10][C:2]([C:31]4[CH:36]=[N:38][NH:29][C:30]=4[CH3:34])=[CH:3][C:4]=3[N:5]=2)[CH:21]2[CH:16]([CH2:17][CH2:18][CH2:19][CH2:20]2)[CH2:15][CH2:14][NH:13]1
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참가 물질

9

반응물 5

HCID 14798Sodium HydroxideHCID 62365Isobutyl chloroformateHCID 12127697N-(t-butoxycarbonyl)-1-carboxy-2-azabicyclo[2.1.1]hexaneHCID 219758623-Amino-5-bromothiophene-2-carboxamideHCID 136333949HCID 136333949, 화합물

생성물 1

HCID 136333947HCID 136333947, 화합물

시약·촉매·용매

3
HCID 887Methanol용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

In the same manner as in Example 71, step A, tert-butyl 1-(6-bromo-4-oxo-3,4-dihydrothieno[3,2-d]pyrimidin-2-yl)octahydroisoquinoline-2 (1H)-carboxylate (180 mg) as a colorless solid from 3-amino-5-bromothiophene-2-carboxamide (0.22 g) produced in Example 1, step D, 2-(tert-butoxycarbonyl)-2-azabicyclo[2.1.1]hexane-1-carboxylic acid (0.57 g), 2-methylpropyl chlorocarbonate (0.27 g), triethylamine (0.20 g) and tetrahydrofuran (10 mL), and 2M aqueous sodium hydroxide solution (1 mL) and methanol (5 mL). In the same manner as in Example 83, step C, 2-(decahydroisoquinolin-1-yl)-6-(5-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4 (3H)-one hydrochloride was obtained from the compound obtained above, tert-butyl 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole-1-carboxylate (270 mg), cesium carbonate (290 mg), [1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloride-dichloromethane complex (1:1)(18 mg), 1,2-dimethoxyethane (10 mL), water (1 mL), and 4M hydrochloric acid/ethyl acetate solution (2 mL) and methanol (10 mL). This was purified by basic silica gel column chromatography (methanol/ethyl acetate) to give the title compound (36 mg) as a colorless solid.

출처 및 근거

ORD 기록
ord-cc4080d345b14cf5932dd64e22a1cfbe
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09388195B2

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