Sodium Bicarbonate → HCID 178502156, compound

HRID 79904Notes

Reaction equation

HRID 79904 reaction equation
[CH3:1][O:2][C:3](=[O:29])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][C:14](=[O:16])[CH2:13][CH:12]1[C:17]1[NH:18][C:19]([C:22]2[CH:27]=[CH:26][C:25](Br)=[CH:24][CH:23]=2)=[CH:20][N:21]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].[CH3:30][O:31][C:32](=[O:69])[NH:33][CH:34]([C:38]([N:40]1[CH2:44][CH2:43][CH2:42][CH:41]1[C:45]1[NH:46][CH:47]=[C:48]([C:50]2[CH:59]=[CH:58][C:57]3[C:52](=[CH:53][CH:54]=[C:55](B4OC(C)(C)C(C)(C)O4)[CH:56]=3)[CH:51]=2)[N:49]=1)=[O:39])[CH:35]([CH3:37])[CH3:36].C(=O)(O)[O-].[Na+]>COCCOC>[CH3:1][O:2][C:3](=[O:29])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][C:14](=[O:16])[CH2:13][CH:12]1[C:17]1[NH:18][C:19]([C:22]2[CH:27]=[CH:26][C:25]([C:55]3[CH:54]=[CH:53][C:52]4[C:57](=[CH:58][CH:59]=[C:50]([C:48]5[N:49]=[C:45]([CH:41]6[CH2:42][CH2:43][CH2:44][N:40]6[C:38](=[O:39])[CH:34]([NH:33][C:32]([O:31][CH3:30])=[O:69])[CH:35]([CH3:37])[CH3:36])[NH:46][CH:47]=5)[CH:51]=4)[CH:56]=3)=[CH:24][CH:23]=2)=[CH:20][N:21]=1)=[O:10])[CH:6]([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 66620390(1-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-oxo-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl esterHCID 178502154HCID 178502154, compound

Product 1

HCID 178502156HCID 178502156, compoundYield 5%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

(1-{2-[5-(4-Bromo-phenyl)-1H-imidazol-2-yl]-4-oxo-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (46.0 mg, 0.1 mmol), [2-Methyl-1-(2-{4-[6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-naphthalen-2-yl]-1H-imidazol-2-yl}-pyrrolidine-1-carbonyl)-propyl]-carbamic acid methyl ester (54 mg, 0.1 mmol), and Pd[PPh3]4 (11.5 mg, 0.01 mmol) were dissolved in DME (2 mL) under an atmosphere of argon. Saturated, aqueous sodium bicarbonate solution (0.3 mL) was added and the reaction was heated under microwave conditions at 120° C. for 20 minutes. The solids were discarded and the volatiles were removed in vacuo. The crude reaction mixture was purified by RP-HPLC (eluent: water/MeCN w/0.1% TFA) to yield the product (4.0 mg) as a TFA salt.

Workup

  1. customthe volatiles were removed in vacuo
  2. customThe crude reaction mixture
  3. customwas purified by RP-HPLC (eluent: water/MeCN w/0.1% TFA)

Sources & evidence

ORD record
ord-49c0d4ddf2164b3990553b0d3cfe9726
Source dataset
uspto-grants-2014_09
Patent number
US08841278B2

Reaction notes

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