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

HRID 1751465Notes

Reaction equation

HRID 1751465 reaction equation
COC(=O)NC(C1CCOCC1)C(N1CC(F)(F)CC1C1NC(C2C=CC(C3C=CC4C(=CC=C(C5NC([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])[C:48]6[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=6)=NC=5)C=4)C=3)=CC=2)=CN=1)=O.[CH3:67][O:68][C:69]([NH:71][CH:72]([CH:76]1[CH2:81]COCC1)[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]([C:107]4[CH:116]=[CH:115][C:114]5[C:109](=[CH:110][CH:111]=[C:112]([C:117]6[NH:118][C:119](C7CCCN7C(OCC7C=CC=CC=7)=O)=[N:120][CH:121]=6)[CH:113]=5)[CH:108]=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]([O:141]C(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>>[CH3:67][O:68][C:69](=[O:70])[NH:71][CH:72]([C:73]([N:89]1[CH:95]([C:96]2[NH:97][C:98]([C:101]3[CH:106]=[CH:105][C:104]([C:107]4[CH:116]=[CH:115][C:114]5[C:109](=[CH:110][CH:111]=[C:112]([C:117]6[NH:118][C:119]([CH:41]7[CH2:45][CH2:44][CH2:43][N:42]7[C:46](=[O:59])[CH:47]([NH:54][C:55]([O:57][CH3:58])=[O:56])[C:48]7[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=7)=[N:120][CH:121]=6)[CH:113]=5)[CH:108]=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:75])[CH:76]([O:141][CH3:137])[CH3:81]

Participants

5

Reactant 4

HCID 585162412-(methoxycarbonylamino)-2-(tetrahydro-2H-pyran-4-yl)acetic acidHCID 69675058HCID 69675058, compoundHCID 69675276HCID 69675276, compoundHCID 86708746HCID 86708746, compound

Product 1

HCID 69675340[2-Methoxy-1-(6-{5-[4-(6-{2-[1-(2-methoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-5-aza-spiro[2.4]heptane-5-carbonyl)-propyl]-carbamic acid methyl esterYield 29%

Procedure

[2-Methoxy-1-(6-{5-[4-(6-{2-[1-(2-methoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-5-aza-spiro[2.4]heptane-5-carbonyl)-propyl]-carbamic acid methyl ester (0.09 g, 29%) was prepared following the procedure for [2-(4,4-Difluoro-2-{5-[4-(6-{2-[1-(2-methoxycarbonylamino-2-phenyl-acetyl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-pyrrolidin-1-yl)-2-oxo-1-(tetrahydro-pyran-4-yl)-ethyl]-carbamic acid methyl ester, substituting 3-Methoxy-2-methoxycarbonylamino-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 C49H52N8O7: 864.40 (M+); Found: 865.97 (M+H+).

Sources & evidence

ORD record
ord-ec2a9988331e4f3d937e0474f8b8d73d
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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