Cesium carbonate → HCID 59427344, compound

HRID 1013673Notes

Reaction equation

HRID 1013673 reaction equation
Cl[C:2]1[CH:3]=[CH:4][N:5]=[C:6]2[C:11]=1[N:10]=[CH:9][C:8]([O:12][CH3:13])=[CH:7]2.[C:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([NH:34][C:35]3[CH:40]=[CH:39][C:38]([OH:41])=[CH:37][CH:36]=3)=[N:26][N:25]=2)=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:27]([NH:34][C:35]3[CH:36]=[CH:37][C:38]([O:41][C:2]4[C:11]5[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][N:10]=5)[N:5]=[CH:4][CH:3]=4)=[CH:39][CH:40]=3)=[N:26][N:25]=2)=[CH:20][CH:19]=1)([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 594273408-Chloro-3-methoxy-1,5-naphthyridineHCID 136381724HCID 136381724, compound

Product 1

HCID 59427344HCID 59427344, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

In a nitrogen purged sealed tube, 8-chloro-3-methoxy-1,5-naphthyridine (0.053 g, 0.271 mmol) was dissolved in DMF (2.00 mL). 4-(4-(4-Tert-butylphenyl)phthalazin-1-ylamino)phenol (0.100 g, 0.271 mmol) and cesium carbonate (0.176 g, 0.541 mol) were added, and the mixture in the tube was stirred at 90° C. for 17 h. Upon cooling to RT, the mixture was concentrated in vacuo, and purified by silica gel chromatography using 0-100% CH2Cl2:MeOH(90:10)/CH2Cl2 to yield 4-(4-tert-butylphenyl)-N-(4-(7-methoxy-1,5-naphthyridin-4-yloxy)phenyl)phthalazin-1-amine as off-white solid. MS [M+H]=528.1; Calc'd 527.6 for C33H29N5O2.

Workup

  1. customIn a nitrogen purged
  2. customsealed tube
  3. temperatureUpon cooling to RT
  4. concentrationthe mixture was concentrated in vacuo
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-8bd665dfdc93455792aaa5f121257e6e
Source dataset
uspto-grants-2011_07
Patent number
US07981891B2

Reaction notes

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