Sodium Carbonate → HCID 59165900, compound

HRID 1442838Notes

Reaction equation

HRID 1442838 reaction equation
CC1(C)C(C)(C)OB([C:9]2[CH:14]=[CH:13][C:12]([CH:15]3[NH:19][C:18](=[O:20])[CH2:17][CH2:16]3)=[CH:11][CH:10]=2)O1.Cl[C:23]1[N:28]=[C:27]([NH:29][C:30]([C:32]2([C:35]3[CH:45]=[CH:44][C:38]4[O:39][C:40]([F:43])([F:42])[O:41][C:37]=4[CH:36]=3)[CH2:34][CH2:33]2)=[O:31])[CH:26]=[CH:25][C:24]=1[CH3:46].C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC>[F:43][C:40]1([F:42])[O:39][C:38]2[CH:44]=[CH:45][C:35]([C:32]3([C:30]([NH:29][C:27]4[CH:26]=[CH:25][C:24]([CH3:46])=[C:23]([C:9]5[CH:10]=[CH:11][C:12]([CH:15]6[CH2:16][CH2:17][C:18](=[O:20])[NH:19]6)=[CH:13][CH:14]=5)[N:28]=4)=[O:31])[CH2:34][CH2:33]3)=[CH:36][C:37]=2[O:41]1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 59165796N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropane-1-carboxamideHCID 591661681004294-99-8

Product 1

HCID 59165900HCID 59165900, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

5-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)pyrrolidin-2-one (43 mg, 0.15 mmol), N-(6-chloro-5-methylpyridin-2-yl)-1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)cyclopropanecarboxamide (37 mg, 0.10 mmol) and Pd(PPh3)4 (6 mg, 0.005 mmol) were placed a reaction tube. DME (1 mL) and saturated aqueous Na2CO3 (100 μL) were added and the reaction vial was stirred under N2 atmosphere at 80° C. overnight. The mixture was filtered and concentrated. The residue was dissolved in DMSO and purified by reverse-phase HPLC to yield 1-(2,2-difluorobenzo[d][1,3]dioxol-5-yl)-N-(5-methyl-6-(4-(5-oxopyrrolidin-2-yl)phenyl)pyridin-2-yl)cyclopropanecarboxamide ESI-MS m/z calc. 491.2, found 492.3 (M+1)+. Retention time 1.75 minutes. 1H NMR (400 MHz, DMSO-d6) δ 8.78 (s, 1H), 8.12 (s, 1H), 7.88 (d, J=8.4 Hz, 1H), 7.72 (d, J=8.5 Hz, 1H), 7.57 (d, J=1.6 Hz, 1H), 7.44-7.34 (m, 6H), 4.71 (t, J=7.1 Hz, 1H), 2.50-2.44 (m, 1H), 2.27-2.23 (m, 5H), 1.81-1.72 (m, 1H), 1.53-1.50 (m, 2H), 1.19-1.16 (m, 2H).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated
  3. dissolutionThe residue was dissolved in DMSO
  4. custompurified by reverse-phase HPLC

Sources & evidence

ORD record
ord-130538c6a8094660ad26e2b9133fbf4c
Source dataset
uspto-grants-2010_02
Patent number
US07659268B2

Reaction notes

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