Cesium carbonate → HCID 86708600, compound

HRID 921721Notes

Reaction equation

HRID 921721 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([N:11]2[CH2:14][CH:13]([N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)[CH2:12]2)[C:9]=1[Cl:10])[C:5]#[N:6].[CH2:22]([N:24](CC1C=CC(OC)=CC=1)[C:25]1[C:30]2=[N:31][CH:32]=[C:33]([C:34]#[N:35])[N:29]2[N:28]=[C:27](S(C)(=O)=O)[N:26]=1)[CH3:23].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:10][C:9]1[C:8]([N:11]2[CH2:12][CH:13]([N:15]3[CH2:16][CH2:17][N:18]([CH3:21])[CH2:19][CH2:20]3)[CH2:14]2)=[CH:7][C:4]([C:5]#[N:6])=[CH:3][C:2]=1[NH:1][C:27]1[N:26]=[C:25]([NH:24][CH2:22][CH3:23])[C:30]2=[N:31][CH:32]=[C:33]([C:34]#[N:35])[N:29]2[N:28]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 86708601HCID 86708601, compoundHCID 86708602HCID 86708602, compound2×

Product 1

HCID 86708600HCID 86708600, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-amino-4-chloro-5-(3-(4-methylpiperazin-1-yl)azetidin-1-yl)benzonitrile (Example 151C) (40 mg, 0.131 mmol), 4-(ethyl(4-methoxybenzyl)amino)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (Intermediate 7) (50.5 mg, 0.131 mmol), and Cs2CO3 (128 mg, 0.392 mmol) in DMF were heated at 45° C. for 14 h. LC/MS showed product formation. The mixture was filtered and rinsed with CH2Cl2, then concentrated and the crude was taken forward to the next reaction.

Workup

  1. filtrationThe mixture was filtered
  2. washrinsed with CH2Cl2
  3. concentrationconcentrated
  4. customthe crude was taken forward to the next reaction

Sources & evidence

ORD record
ord-78b85bb4fb8b46469aa1645bd53dc16a
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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