HCID 69675210, compound → (R)-2-((1R,3S,4R)-3-(6-(9,9-difluoro-7-(2-((S)-1-((2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-2-oxo-1-phenylethylcarbamic acid methyl ester

HRID 1751553Notes

Reaction equation

COC(=O)N[C@@H](C(C)C)C(N1[C@H](C2NC(C3C=CC(C4C=CC5C(=CC=C(C6NC([C@@H]7CCCN7[C:48](=[O:61])[C@H:49]([NH:56][C:57]([O:59][CH3:60])=[O:58])[C:50]7[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=7)=NC=6)C=5)C=4)=CC=3)=CN=2)CC2(OCCO2)C1)=O.Cl.Cl.Cl.[C@H:69]12[CH2:75][C@@H:72]([CH2:73][CH2:74]1)[C@@H:71]([C:76]1[NH:80][C:79]3[CH:81]=[C:82]([C:85]4[CH:97]=[C:96]5[C:88]([C:89]6[CH:90]=[CH:91][C:92]([C:100]7[NH:104][C:103]([C@@H:105]8[CH2:109][CH2:108][CH2:107][N:106]8[C:110](=[O:121])[C@@H:111]([NH:116][C:117](=[O:120])[O:118][CH3:119])[C@H:112]([O:114][CH3:115])[CH3:113])=[N:102][CH:101]=7)=[CH:93][C:94]=6[C:95]5([F:99])[F:98])=[CH:87][CH:86]=4)[CH:83]=[CH:84][C:78]=3[N:77]=1)[NH:70]2>>[CH3:60][O:59][C:57](=[O:58])[NH:56][C@H:49]([C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)[C:48]([N:70]1[C@H:71]([C:76]2[NH:80][C:79]3[CH:81]=[C:82]([C:85]4[CH:86]=[CH:87][C:88]5[C:89]6[C:94](=[CH:93][C:92]([C:100]7[NH:104][C:103]([C@@H:105]8[CH2:109][CH2:108][CH2:107][N:106]8[C:110](=[O:121])[C@@H:111]([NH:116][C:117]([O:118][CH3:119])=[O:120])[C@H:112]([O:114][CH3:115])[CH3:113])=[N:102][CH:101]=7)=[CH:91][CH:90]=6)[C:95]([F:99])([F:98])[C:96]=5[CH:97]=4)[CH:83]=[CH:84][C:78]=3[N:77]=2)[C@H:72]2[CH2:75][C@H:69]1[CH2:74][CH2:73]2)=[O:61]

Participants

Reactant 2

HCID 69675210HCID 69675210, compound

HCID 131733619methyl (2S,3R)-1-((S)-2-(5-(7-(2-((1R,3 S,4R)-2-azabicyclo[2.2.1]heptan-3-yl)-1H-benzo[d]imidazol-6-yl)-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methoxy-1-oxobutan-2-ylcarbamate 3HCl salt

Product 1

HCID 89917763(R)-2-((1R,3S,4R)-3-(6-(9,9-difluoro-7-(2-((S)-1-((2S,3R)-3-methoxy-2-(methoxycarbonylamino)butanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)-9H-fluoren-2-yl)-1H-benzo[d]imidazol-2-yl)-2-azabicyclo[2.2.1]heptan-2-yl)-2-oxo-1-phenylethylcarbamic acid methyl ester

Procedure

The title compound was prepared according to the method employed to prepare (S)-1-((S)-8-(5-(4-(6-(2-((S)-1-((R)-2-(methoxycarbonylamino)-2-phenylacetyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-3-methyl-1-oxobutan-2-ylcarbamic acid methyl ester, except that methyl (2S,3R)-1-((S)-2-(5-(7-(2-((1R,3S,4R)-2-azabicyclo[2.2.1]heptan-3-yl)-1H-benzo[d]imidazol-6-yl)-9,9-difluoro-9H-fluoren-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methoxy-1-oxobutan-2-ylcarbamate 3HCl salt was used instead of methyl (S)-3-methyl-1-oxo-1-((S)-8-(5-(4-(6-(2-((S)-pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)butan-2-ylcarbamate 3HCl salt. MS (ESI) m/z 913.69 [M+H]+. (93 mg, 57%).

Sources & evidence

ORD record: ord-253b736acf45444fb0fda705e09124e7
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09156823B2

Reaction notes

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