Ethanol → tert-butyl 2-[[3-methyl-2-[5-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonyl-3-pyridinyl]phenyl]methoxy]acetate

HRID 723092노트

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HRID 723092 반응식
[C:1]([O:5][C:6](=[O:26])[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1B1OC(C)(C)C(C)(C)O1)([CH3:4])([CH3:3])[CH3:2].[C:27]([O:31][C:32](=[O:53])[NH:33][C:34]([C:36]1[S:37][C:38]([S:51][CH3:52])=[C:39]([S:41]([C:44]2[CH:45]=[N:46][CH:47]=[C:48](Br)[CH:49]=2)(=[O:43])=[O:42])[CH:40]=1)=[NH:35])([CH3:30])([CH3:29])[CH3:28].C([O-])([O-])=O.[Na+].[Na+].C(O)C>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.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:26])[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([CH3:16])[C:11]=1[C:48]1[CH:47]=[N:46][CH:45]=[C:44]([S:41]([C:39]2[CH:40]=[C:36]([C:34]([NH:33][C:32]([O:31][C:27]([CH3:28])([CH3:29])[CH3:30])=[O:53])=[NH:35])[S:37][C:38]=2[S:51][CH3:52])(=[O:43])=[O:42])[CH:49]=1)([CH3:2])([CH3:3])[CH3:4]

참가 물질

8

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 69586495[3-Methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-acetic acid tert-butyl esterHCID 145857652tert-butyl N-[4-[(5-bromo-3-pyridinyl)sulfonyl]-5-methylsulfanylthiophene-2-carboximidoyl]carbamate

생성물 1

HCID 145857618tert-butyl 2-[[3-methyl-2-[5-[5-[N-[(2-methylpropan-2-yl)oxycarbonyl]carbamimidoyl]-2-methylsulfanylthiophen-3-yl]sulfonyl-3-pyridinyl]phenyl]methoxy]acetate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

The procedure as in Example 1: step c was followed using [3-Methyl-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyloxy]-acetic acid tert-butyl ester (252.2 mg, 0.62 mmol, Example 131: step d), {[4-(5-Bromo-pyridine-3-sulfonyl)-5-methylsulfanyl-thiophen-2-yl]-imino-methyl}-carbamic acid tert-butyl ester (75.9 mg, 0.15 mmol, Example 128: step a), Pd(PPh3)4 (35 mg, 0.03 mmol), aqueous Na2CO3 (2M, 1 mL), ethanol (1 mL) and toluene (2 mL). The reaction was heated to 80° C. for 24 hours. The reaction mixture was dissolved into EtOAc and washed with brine. The organic layers were dried (MgSO4) and removal of the solvents in vacuo was followed by purification by flash column chromatography (SiO2) (30% EtOAc in hexanes) of the residue yielded the title compound (460 mg) as a brown oil. ESI-MS (m/z): Calcd. for C30H37N3O7S3: 648.2 (M+1) found: 647.9.

후처리

  1. washwashed with brine
  2. customThe organic layers were dried
  3. custom(MgSO4) and removal of the solvents in vacuo
  4. customwas followed by purification by flash column chromatography (SiO2) (30% EtOAc in hexanes) of the residue

출처 및 근거

ORD 기록
ord-2df6961ccc8b4b51984e60ed57441395
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07138530B2

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