tert-butyl (2S)-2-[5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylate → HCID 178502153, compound

HRID 1751521Notes

Reaction equation

HRID 1751521 reaction equation
C(OC(N1CC(=C)CC1C1NC(C2C=CC(C3C=CC4C(=CC=C(C5NC(C6CCCN6C(=O)C(NC(OC)=O)C(C)C)=NC=5)C=4)C=3)=CC=2)=CN=1)=O)(C)(C)C.[C:56]([O:60][C:61]([N:63]1[CH2:67][CH2:66][CH2:65][CH:64]1[C:68]1[NH:69][C:70]([C:73]2[CH:82]=[CH:81][C:80]3[C:75](=[CH:76][CH:77]=[C:78](Br)[CH:79]=3)[CH:74]=2)=[CH:71][N:72]=1)=[O:62])([CH3:59])([CH3:58])[CH3:57].[CH3:84][O:85][C:86](=[O:121])[NH:87][CH:88]([C:92]([N:94]1[CH2:98][CH2:97][CH2:96][CH:95]1[C:99]1[NH:103][C:102]2[C:104]3[C:109]([CH2:110][CH2:111][C:101]=2[N:100]=1)=[CH:108][C:107](B1OC(C)(C)C(C)(C)O1)=[CH:106][CH:105]=3)=[O:93])[CH:89]([CH3:91])[CH3:90]>>[C:56]([O:60][C:61]([N:63]1[CH2:67][CH2:66][CH2:65][CH:64]1[C:68]1[NH:69][C:70]([C:73]2[CH:82]=[CH:81][C:80]3[C:75](=[CH:76][CH:77]=[C:78]([C:107]4[CH:108]=[C:109]5[C:104](=[CH:105][CH:106]=4)[C:102]4[NH:103][C:99]([CH:95]6[CH2:96][CH2:97][CH2:98][N:94]6[C:92](=[O:93])[CH:88]([NH:87][C:86]([O:85][CH3:84])=[O:121])[CH:89]([CH3:91])[CH3:90])=[N:100][C:101]=4[CH2:111][CH2:110]5)[CH:79]=3)[CH:74]=2)=[CH:71][N:72]=1)=[O:62])([CH3:59])([CH3:58])[CH3:57]

Participants

4

Reactant 3

HCID 58185449tert-butyl (2S)-2-[5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl]pyrrolidine-1-carboxylateHCID 696727712-{5-[4-(6-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-4-methylene-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178502148HCID 178502148, compound

Product 1

HCID 178502153HCID 178502153, compoundYield 74%

Procedure

This compound was synthesized using the procedure used to make 2-{5-[4-(6-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-3H-imidazol-4-yl}-naphthalen-2-yl)-phenyl]-1H-imidazol-2-yl}-4-methylene-pyrrolidine-1-carboxylic acid tert-butyl ester using 2-[5-(6-Bromo-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.641 g, 1.449 mmol) and (2-Methyl-1-{2-[7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-4,5-dihydro-1H-naphtho[1,2-d]imidazol-2-yl]-pyrrolidine-1-carbonyl}-propyl)-carbamic acid methyl ester (1.06 g, 2.029 mmol) to give 2-[5-(6-{2-[1-(2-Methoxycarbonylamino-3-methyl-butyryl)-pyrrolidin-2-yl]-4,5-dihydro-1H-naphtho[1,2-d]imidazol-7-yl}-naphthalen-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carboxylic acid tert-butyl ester (0.812 g, 74% yield) as a solid. LCMS-ESI+: calc'd for C44H51N7O5: 757.40 (M+); Found: 758.75 (M+H+).

Workup

  1. customThis compound was synthesized

Sources & evidence

ORD record
ord-273a7189c43d42f9b7d670b871e652fe
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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