2-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acid → [1-(2-{5-[6-(4-{2-[5-(2-Methoxycarbonylamino-2-phenyl-acetyl)-5-aza-spiro[2.4]hept-6-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester

HRID 1751462Notes

Reaction equation

HRID 1751462 reaction equation
COC(=O)NC(C1C=CC=CC=1)C(N1CC(F)(F)CC1C1NC(C2C=CC([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[C:31]([C:36]5[NH:37][C:38]([CH:41]6[CH2:45][CH2:44][CH2:43][N:42]6[C:46](=[O:59])[CH:47]([NH:54][C:55]([O:57][CH3:58])=[O:56])[CH:48]6[CH2:53]COC[CH2:49]6)=[N:39][CH:40]=5)[CH:32]=4)[CH:27]=3)=CC=2)=CN=1)=O.[CH3:67][O:68][C:69]([NH:71][CH:72]([CH:76]1[CH2:81][CH2:80]O[CH2:78][CH2:77]1)[C:73]([OH:75])=O)=[O:70].C(OC([N:89]1[CH:95]([C:96]2[NH:97][C:98]([C:101]3[CH:106]=[CH:105][C:104](C4C=CC5C(=CC=C(C6NC(C7CCCN7C(OCC7C=CC=CC=7)=O)=NC=6)C=5)C=4)=[CH:103][CH:102]=3)=[CH:99][N:100]=2)[CH2:94][C:91]2([CH2:93][CH2:92]2)[CH2:90]1)=O)(C)(C)C.[C:137](OC(N1CC(F)(F)CC1C1NC(C2C=CC(C3C=CC4C(=CC=C(C5NC(C6CCCN6C(OCC6C=CC=CC=6)=O)=NC=5)C=4)C=3)=CC=2)=CN=1)=O)(C)(C)C>>[CH3:58][O:57][C:55](=[O:56])[NH:54][CH:47]([C:46]([N:42]1[CH2:43][CH2:44][CH2:45][CH:41]1[C:38]1[NH:37][C:36]([C:31]2[CH:30]=[CH:29][C:28]3[C:27](=[CH:26][CH:35]=[C:34]([C:104]4[CH:103]=[CH:102][C:101]([C:98]5[NH:97][C:96]([CH:95]6[CH2:94][C:91]7([CH2:92][CH2:93]7)[CH2:90][N:89]6[C:73](=[O:75])[CH:72]([NH:71][C:69]([O:68][CH3:67])=[O:70])[C:76]6[CH:77]=[CH:78][CH:137]=[CH:80][CH:81]=6)=[N:100][CH:99]=5)=[CH:106][CH:105]=4)[CH:33]=3)[CH:32]=2)=[CH:40][N:39]=1)=[O:59])[CH:48]([CH3:49])[CH3:53]

Participants

5

Reactant 4

HCID 585162412-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acidHCID 69675058HCID 69675058, compoundHCID 69675276HCID 69675276, compoundHCID 86708747HCID 86708747, compound

Product 1

HCID 69675484[1-(2-{5-[6-(4-{2-[5-(2-Methoxycarbonylamino-2-phenyl-acetyl)-5-aza-spiro[2.4]hept-6-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl esterYield 28%

Procedure

[1-(2-{5-[6-(4-{2-[5-(2-Methoxycarbonylamino-2-phenyl-acetyl)-5-aza-spiro[2.4]hept-6-yl]-3H-imidazol-4-yl}-phenyl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-2-methyl-propyl]-carbamic acid methyl ester (0.08 g, 28%) was prepared following the procedure for {2-[4,4-Difluoro-2-(5-{4-[6-(2-{1-[2-methoxycarbonylamino-2-(tetrahydro-pyran-4-yl)-acetyl]-pyrrolidin-2-yl}-3H-imidazol-4-yl)-naphthalen-2-yl]-phenyl}-1H-imidazol-2-yl)-pyrrolidin-1-yl]-2-oxo-1-phenyl-ethyl}-carbamic acid methyl ester, substituting 2-Methoxycarbonylamino-3-methyl-butyric acid for Methoxycarbonylamino-(tetrahydro-pyran-4-yl)-acetic acid and 6-[5-(4-{6-[2-(1-Benzyloxycarbonyl-pyrrolidin-2-yl)-3H-imidazol-4-yl]-naphthalen-2-yl}-phenyl)-1H-imidazol-2-yl]-5-aza-spiro[2.4]heptane-5-carboxylic acid tert-butyl ester for 2-[5-(4-{6-[2-(1-Benzyloxycarbonyl-pyrrolidin-2-yl)-3H-imidazol-4-yl]-naphthalen-2-yl}-phenyl)-1H-imidazol-2-yl]-4,4-difluoro-pyrrolidine-1-carboxylic acid tert-butyl ester. LCMS-ESI+: calc'd for C49H52N8O6: 848.40 (M+); Found: 849.95 (M+H+).

Sources & evidence

ORD record
ord-a36483994ff94b71a48833983b95072e
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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