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Sodium Hydroxide → HCID 136333947、化合物

HRID 1409062
ノート
印刷プレビュー

反応式

HRID 1409062 の反応式
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
参加物実験手順出典と根拠反応ノート

参加物

9

反応物 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、化合物

生成物 1

HCID 136333947HCID 136333947、化合物

試薬・触媒・溶媒

3
HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

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.

出典と根拠

ORDレコード
ord-c9f918c3955f4e98a2232ae2cc958a6b
出典データセット
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08921354B2

反応ノート

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