Potassium Carbonate → (S)-1-((S)-2-(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)thiazolidin-3-yl)-3-methyl-1-oxobutan-2-ylcarbamic acid methyl ester

HRID 1751565Notes

Reaction equation

HRID 1751565 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]1[NH:16][C:15]([C@@H:17]3[CH2:21][CH2:20][CH2:19][N:18]3[C:22](=[O:35])[C@H:23]([NH:30][C:31](=[O:34])[O:32][CH3:33])[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[N:14][CH:13]=1)[CH:6]=[CH:5]2.CC(C)[C@H:38]([NH:66][C:67](=[O:70])[O:68][CH3:69])[C:39](=[O:65])[N:40]1[CH2:44][CH2:43][S:42][C@H:41]1[C:45]1[NH:46][C:47]([C:50]2[CH:55]=[CH:54][C:53](B3OC(C)(C)C(C)(C)O3)=[CH:52][CH:51]=2)=[CH:48][N:49]=1.[C:72]([O-])([O-])=O.[K+].[K+].O1[CH2:83][CH2:82]OCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:69][O:68][C:67](=[O:70])[NH:66][C@@H:38]([CH:82]([CH3:83])[CH3:72])[C:39]([N:40]1[CH2:44][CH2:43][S:42][C@H:41]1[C:45]1[NH:46][C:47]([C:50]2[CH:51]=[CH:52][C:53]([C:2]3[CH:11]=[CH:10][C:9]4[C:4](=[CH:5][CH:6]=[C:7]([C:12]5[NH:16][C:15]([C@@H:17]6[CH2:21][CH2:20][CH2:19][N:18]6[C:22](=[O:35])[C@H:23]([NH:30][C:31]([O:32][CH3:33])=[O:34])[C:24]6[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=6)=[N:14][CH:13]=5)[CH:8]=4)[CH:3]=3)=[CH:54][CH:55]=2)=[CH:48][N:49]=1)=[O:65]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 86708773HCID 86708773, compoundHCID 86708774HCID 86708774, compound

Product 1

HCID 69675635(S)-1-((S)-2-(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)thiazolidin-3-yl)-3-methyl-1-oxobutan-2-ylcarbamic acid methyl ester

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Methyl (R)-2-((S)-2-(5-(6-bromonaphthalen-2-yl)-1H-imidazol-2-yl)pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate (155 mg, 0.29 mmol), methyl (S)-3-methyl-1-oxo-1-((S)-2-(5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-imidazol-2-yl)thiazolidin-3-yl)butan-2-ylcarbamate (195 mg, 0.37 mmol), Pd(dppf)Cl2 (43 mg, 0.058 mmol) and 2M K2CO3 (320 uL, 0.64 mmol) were all dissolved in 1,4-dioxane (1.5 mL) and the mixture was bubbled with nitrogen gas for 5 minutes. The vessel was capped, sealed and placed in an oil bath at 95° C. for 3 hours.

Workup

  1. customthe mixture was bubbled with nitrogen gas for 5 minutes
  2. customThe vessel was capped
  3. customsealed

Sources & evidence

ORD record
ord-913f7264ad83483589cc636e070a0f7b
Source dataset
uspto-grants-2015_10
Patent number
US09156823B2

Reaction notes

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