Sodium Carbonate → HCID 131732640, compound

HRID 881987Notes

Reaction equation

HRID 881987 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][C:16](=[O:30])[C:17]3[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH2:26][CH:27]4[CH2:29][CH2:28]4)[CH:18]=3)[CH2:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.CC1(C)C(C)(C)OB([C:39]2[CH:40]=[C:41]([C:45]3[N:46]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[CH:47]=[CH:48][N:49]=3)[CH:42]=C[CH:44]=2)O1.C([O-])([O-])=O.[Na+].[Na+].CC#[N:67].O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH:27]1([CH2:26][O:25][C:19]2[CH:18]=[C:17]([CH:22]=[C:21]([O:23][CH3:24])[CH:20]=2)[C:16]([NH:15][CH2:14][CH:11]2[CH2:10][CH2:9][N:8]([C:6]3[N:67]=[C:4]([C:5]4[CH:44]=[CH:39][CH:40]=[C:41]([C:45]5[N:46]([CH2:50][O:51][CH2:52][CH2:53][Si:54]([CH3:57])([CH3:56])[CH3:55])[CH:47]=[CH:48][N:49]=5)[CH:42]=4)[N:3]=[CH:2][N:7]=3)[CH2:13][CH2:12]2)=[O:30])[CH2:29][CH2:28]1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 18373917Acetonitrile--water (1/1)HCID 71302438HCID 71302438, compoundHCID 117677260HCID 117677260, compound

Product 1

HCID 131732640HCID 131732640, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Conditions

Temperature
150 °C

Procedure

To a solution of N-((1-(4-chloro-1,3,5-triazin-2-yl)piperidin-4-yl)methyl)-3-(cyclopropylmethoxy)-5-methoxybenzamide (Example 31, step v, 150 mg, 0.35 mmol) in CH3CN H2O (4 ml, 3/1) were added 2-(3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (Example 9, 140 mg, 0.35 mmol), Na2CO3 (73 mg, 0.70 mmol) and Pd(PPh3)2Cl2 (12 mg, 0.018 mmol) under a nitrogen atmosphere. The reaction mixture was stirred at 150° C. for 10 minutes in a microwave reactor. After cooling to room temperature the mixture was filtered, the filtrate dried over Na2SO4 and the solvents were removed under reduced pressure. The residue was purified by using prep HPLC to give 3-(cyclopropylmethoxy)-5-methoxy-N-((1-(4-(3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)phenyl)-1,3,5-triazin-2-yl)piperidin-4-yl)methyl)benzamide (35 mg) as a solid.

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. filtrationwas filtered
  3. dry with materialthe filtrate dried over Na2SO4
  4. customthe solvents were removed under reduced pressure
  5. customThe residue was purified

Sources & evidence

ORD record
ord-b490b70fbc42473d99495e28caaf4213
Source dataset
uspto-grants-2015_03
Patent number
US08993757B2

Reaction notes

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