Cesium carbonate → HCID 86708538, compound

HRID 1430849Notes

Reaction equation

HRID 1430849 reaction equation
[CH:1]1([N:4](CC2C=CC(OC)=CC=2)[C:5]2[C:10]3=[N:11][CH:12]=[C:13]([C:14]#[N:15])[N:9]3[N:8]=[C:7](S(C)(=O)=O)[N:6]=2)[CH2:3][CH2:2]1.[NH2:29][C:30]1[CH:31]=[C:32]([CH:35]=[C:36]([N:39]2[CH2:44][CH2:43][O:42][CH:41]([C:45]([N:47]3[CH2:52][CH2:51][O:50][CH2:49][CH2:48]3)=[O:46])[CH2:40]2)[C:37]=1[Cl:38])[C:33]#[N:34].C([O-])([O-])=O.[Cs+].[Cs+].C(=O)(O)[O-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[Cl:38][C:37]1[C:36]([N:39]2[CH2:44][CH2:43][O:42][CH:41]([C:45]([N:47]3[CH2:48][CH2:49][O:50][CH2:51][CH2:52]3)=[O:46])[CH2:40]2)=[CH:35][C:32]([C:33]#[N:34])=[CH:31][C:30]=1[NH:29][C:7]1[N:6]=[C:5]([NH:4][CH:1]2[CH2:2][CH2:3]2)[C:10]2=[N:11][CH:12]=[C:13]([C:14]#[N:15])[N:9]2[N:8]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 86708519HCID 86708519, compoundHCID 867085363-Amino-4-chloro-5-(2-(morpholine-4-carbonyl)morpholino)benzonitrile

Product 1

HCID 86708538HCID 86708538, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 4-(cyclopropyl(4-methoxybenzyl)amino)-2-(methylsulfonyl)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (38.6 mg, 0.097 mmol), 3-amino-4-chloro-5-(2-(morpholine-4-carbonyl)morpholino)benzonitrile (34 mg, 0.097 mmol) and Cs2CO3 (63.2 mg, 0.194 mmol) in DMF (692 μl) up was heated at 50° C. for 4 h. After cooling to rt ON, the reaction mixture was transferred to a separatory funnel containing ethyl acetate and saturated aqueous sodium bicarbonate. The aqueous layer was extracted with ethyl acetate (3×). The combined organics were washed with 10% lithium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Material carried forward as is.

Workup

  1. temperatureAfter cooling to rt ON, the reaction mixture
  2. customwas transferred to a separatory funnel
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×)
  4. washThe combined organics were washed with 10% lithium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a73131d6de5c40999fea147b6159ddfb
Source dataset
uspto-grants-2015_01
Patent number
US08940736B2

Reaction notes

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