Ethanol → tert-butyl N-[4-[3-(3-amino-5-methyl-4-pyridinyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

HRID 2216063

反応式

HRID 2216063 の反応式
C(OC(=O)[NH:7][C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH3:15])[C:13]=1I)(C)(C)C.[C:17]([O:21][C:22](=[O:45])[NH:23][C:24]([C:26]1[S:27][C:28]([S:43][CH3:44])=[C:29]([S:31]([C:34]2[CH:39]=[CH:38][C:37](O)=[C:36](B)[C:35]=2O)(=[O:33])=[O:32])[CH:30]=1)=[NH:25])([CH3:20])([CH3:19])[CH3:18].C(O)C.C1(C)C=CC=CC=1>C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[C:17]([O:21][C:22](=[O:45])[NH:23][C:24]([C:26]1[S:27][C:28]([S:43][CH3:44])=[C:29]([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[C:36]([C:13]3[C:12]([CH3:15])=[CH:11][N:10]=[CH:9][C:8]=3[NH2:7])[CH:35]=2)(=[O:33])=[O:32])[CH:30]=1)=[NH:25])([CH3:20])([CH3:19])[CH3:18]

参加物

8

反応物 4

HCID 702EthanolHCID 1140TolueneHCID 60026355(4-Iodo-5-methyl-pyridin-3-yl)-carbamic acid tert-butyl esterHCID 178419158HCID 178419158、化合物

生成物 1

HCID 145857697tert-butyl N-[4-[3-(3-amino-5-methyl-4-pyridinyl)phenyl]sulfonyl-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒

実験手順

(4-Iodo-5-methyl-pyridin-3-yl)-carbamic acid tert-butyl ester (106 mg, 0.32 mmol, Example 139: step b), {[4-(3-Boranyl-dihydroxy-benzenesulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (145 mg, 0.32 mmol, Example 140: step a) and Pd(PPh3)4 (74 mg, 0.06 mmol) were combined in aqueous Na2CO3 (2M, 1.2 mL), ethanol (1.2 mL) and toluene (2.4 mL) and was heated to 80° C. overnight. The reaction mixture was dissolved into EtOAc and washed with brine. The organic layers were dried (MgSO4) and solvents were removed in vacuo. Purification by flash column chromatography (40% EtOAc/hexanes) afforded the title compound. ESI-MS (m/z): Calcd. for C28H34N4O6S3: 619.2 (M+1); found: 618.8.

後処理

  1. washwashed with brine
  2. dry with materialThe organic layers were dried (MgSO4) and solvents
  3. customwere removed in vacuo
  4. customPurification by flash column chromatography (40% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-bdac16c0a6e84c5b98a1a9d6d963f622
出典データセット
uspto-grants-2006_09
特許番号
US07109354B2

関連ノート

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