2-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-5-tributylstannanyl-imidazole-1-carboxylic acid tert-butyl ester → (S)-2-{5-[5-(4-{2-[(S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-thieno[3,2-b]thiophen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 716539노트

반응식

HRID 716539 반응식
[CH3:1][O:2][C:3](=[O:36])[NH:4][C@H:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[C:16]1[NH:17][C:18]([C:21]2[CH:26]=[CH:25][C:24]([C:27]3[S:31][C:30]4[CH:32]=[C:33](Br)[S:34][C:29]=4[CH:28]=3)=[CH:23][CH:22]=2)=[CH:19][N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].C(OC([N:44]1[C:48]([Sn](CCCC)(CCCC)CCCC)=[CH:47][N:46]=[C:45]1[C@@H:62]1[CH2:66][CH2:65][CH2:64][N:63]1[C:67]([O:69][C:70]([CH3:73])([CH3:72])[CH3:71])=[O:68])=O)(C)(C)C>C1(C)C=CC=CC=1.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>[C:70]([O:69][C:67]([N:63]1[CH2:64][CH2:65][CH2:66][C@H:62]1[C:45]1[NH:46][C:47]([C:33]2[S:34][C:29]3[CH:28]=[C:27]([C:24]4[CH:25]=[CH:26][C:21]([C:18]5[NH:17][C:16]([C@@H:12]6[CH2:13][CH2:14][CH2:15][N:11]6[C:9](=[O:10])[C@@H:5]([NH:4][C:3]([O:2][CH3:1])=[O:36])[CH:6]([CH3:8])[CH3:7])=[N:20][CH:19]=5)=[CH:22][CH:23]=4)[S:31][C:30]=3[CH:32]=2)=[CH:48][N:44]=1)=[O:68])([CH3:73])([CH3:71])[CH3:72]

참가 물질

5

반응물 2

HCID 672401812-((S)-1-tert-butoxycarbonyl-pyrrolidin-2-yl)-5-tributylstannanyl-imidazole-1-carboxylic acid tert-butyl esterHCID 68330854[(S)-1-((S)-2-{5-[4-(5-bromo-thieno[3,2-b]thiophen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

생성물 1

HCID 67240543(S)-2-{5-[5-(4-{2-[(S)-1-((S)-2-methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-phenyl)-thieno[3,2-b]thiophen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carboxylic acid tert-butyl ester수율 43%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

A mixture of compound 62 (0.131 mmol), compound 61 (0.141 mmol), and Pd(PPh3)4 (0.017 mmol) was refluxed in dry toluene under nitrogen overnight. Solvent was removed under reduced pressure. The residue was purified by silica gel chromatography (eluent: DCM to DCM/MeOH 5%) to give compound 63 as an orange solid in 43% yield. MS (ESI, EI+) m/z=744.6 (MH+).

후처리

  1. customSolvent was removed under reduced pressure
  2. customThe residue was purified by silica gel chromatography (eluent: DCM to DCM/MeOH 5%)

출처 및 근거

ORD 기록
ord-e1a5207cf55c48bea8e5ac96ad4af01b
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09187496B2

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