Bis(pinacolato)diborane → (R)-tert-butyl 4-(5-(4-(6-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)oxazolidine-3-carboxylate

HRID 1751566Notes

Reaction equation

HRID 1751566 reaction equation
[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:54]([CH3:56])[CH3:55])[C:7]([N:9]1[C@H:17]([C:18]2[NH:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([C:29]4[CH:30]=[C:31]5C(=CC=4)C4NC([C@@H]6CCCN6C(OC(C)(C)C)=O)=NC=4[CH:33]=[CH:32]5)=[CH:25][CH:24]=3)=[CH:21][N:22]=2)[CH2:16][C:11]2(OCCO2)[CH2:10]1)=[O:8])=[O:4].Br[C:58]1C=C2C(=C[CH:67]=1)C=C(C1NC([C@@H]3CCCN3C(=O)[C@@H](NC(=O)OC)C(C)C)=NC=1)C=C2.BrC1C=C[C:93]([C:96]2[NH:100][C:99]([C@@H:101]3[CH2:105][O:104][CH2:103][N:102]3[C:106]([O:108][C:109]([CH3:112])([CH3:111])[CH3:110])=[O:107])=[N:98][CH:97]=2)=[CH:92][CH:91]=1.BrC1C=CC(C2NC([C@@H]3CC4(OCCO4)CN3C(=O)[C@@H](NC(=O)OC)C(C)C)=NC=2)=CC=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.BrC1C=C2C(=CC=1)C1NC([C@@H]3CCCN3C(OC(C)(C)C)=O)=NC=1C=C2>>[CH3:1][O:2][C:3]([NH:5][C@@H:6]([CH:54]([CH3:55])[CH3:56])[C:7]([N:9]1[CH2:10][CH2:11][CH2:16][C@H:17]1[C:18]1[NH:19][C:20]([C:23]2[CH:28]=[C:27]3[C:26](=[CH:25][CH:24]=2)[CH:29]=[C:30]([C:31]2[CH:91]=[CH:92][C:93]([C:96]4[NH:100][C:99]([C@@H:101]5[CH2:105][O:104][CH2:103][N:102]5[C:106]([O:108][C:109]([CH3:112])([CH3:111])[CH3:110])=[O:107])=[N:98][CH:97]=4)=[CH:33][CH:32]=2)[CH:67]=[CH:58]3)=[CH:21][N:22]=1)=[O:8])=[O:4]

Participants

7

Reactant 6

HCID 2733548Bis(pinacolato)diboraneHCID 59610262methyl (S)-1-((S)-2-(5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamateHCID 59610362((S)-1-{(S)-8-[4-(4-Bromo-phenyl)-1H-imidazol-2-yl]-1,4-dioxa-7-aza-spiro[4.4]nonane-7-carbonyl}-2-methyl-propyl)-carbamic acid methyl esterHCID 69675519(R)-tert-butyl 4-(5-(4-bromophenyl)-1H-imidazol-2-yl)oxazolidine-3-carboxylateHCID 178451893(S)-tert-butyl 2-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylateHCID 178502289HCID 178502289, compound

Product 1

HCID 69675250(R)-tert-butyl 4-(5-(4-(6-(2-((S)-1-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)pyrrolidin-2-yl)-1H-imidazol-5-yl)naphthalen-2-yl)phenyl)-1H-imidazol-2-yl)oxazolidine-3-carboxylate

Procedure

The title compound was prepared according to the method employed to prepare (S)-Tert-butyl 2-(7-(4-(2-((S)-7-((S)-2-(methoxycarbonylamino)-3-methylbutanoyl)-1,4-dioxa-7-azaspiro[4.4]nonan-8-yl)-1H-imidazol-5-yl)phenyl)-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate, except that, respectively, methyl (S)-1-((S)-2-(5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamate and (R)-tert-butyl 4-(5-(4-bromophenyl)-1H-imidazol-2-yl)oxazolidine-3-carboxylate were used instead of methyl (S)-1-((S)-8-(5-(4-bromophenyl)-1H-imidazol-2-yl)-1,4-dioxa-7-azaspiro[4.4]nonan-7-yl)-3-methyl-1-oxobutan-2-ylcarbamate (100 mg, 0.197 mmol), bis(pinacolato)diboron and (S)-tert-butyl 2-(7-bromo-1H-naphtho[1,2-d]imidazol-2-yl)pyrrolidine-1-carboxylate. MS (ESI) m/z 734.91 [M+H]+. (110 mg, 45%).

Sources & evidence

ORD record
ord-43315b0e73c743e194be5c1df6edd8d9
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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