Potassium Carbonate → (S)-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-3-(2-methoxyphenyl)-8-methyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepine-1-carboxamide

HRID 535958Notes

Reaction equation

HRID 535958 reaction equation
Br[C:2]1[N:6]2[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][C:5]2=[C:4]([C:13]([NH:15][C@@H:16]([C:21]([CH3:24])([CH3:23])[CH3:22])[C:17]([NH:19][CH3:20])=[O:18])=[O:14])[N:3]=1.[CH3:25][O:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH3:22][C:21]([CH3:24])([CH3:23])[C@H:16]([NH:15][C:13]([C:4]1[N:3]=[C:2]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[O:26][CH3:25])[N:6]2[CH2:7][CH2:8][CH2:9][N:10]([CH3:12])[CH2:11][C:5]=12)=[O:14])[C:17]([NH:19][CH3:20])=[O:18]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27339582-Methoxyphenylboronic acidHCID 57635118HCID 57635118, compound

Product 1

HCID 57635134(S)-N-(3,3-dimethyl-1-(methylamino)-1-oxobutan-2-yl)-3-(2-methoxyphenyl)-8-methyl-6,7,8,9-tetrahydro-5H-imidazo[1,5-a][1,4]diazepine-1-carboxamide

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
100 °C

Procedure

A mixture of Compound 324 (7.7 mg), 2-methoxyphenylboronic acid (0.038 mmol), palladium tetrakis(triphenylphosphine) (2.5 mg) and potassium carbonate (3 mg) in dioxane/water was heated at 100° C. for two hours. The mixture was filtered through a thiol-based palladium scavenger and purified by preparative LC-MS to give Compound 325. LCMS (+ESI) m/z 428.2 [M+H]+.

Workup

  1. filtrationThe mixture was filtered through a thiol-
  2. custompurified by preparative LC-MS

Sources & evidence

ORD record
ord-c32f99edf0d648e0bf44618abf911a59
Source dataset
uspto-grants-2014_10
Patent number
US08859538B2

Reaction notes

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