Cesium carbonate → HCID 118114929, compound

HRID 1050621Notes

Reaction equation

HRID 1050621 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][C@@H:9]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[CH2:10]2)[CH:5]=[N:4][C:3]=1[C:21]#[N:22].Cl.[CH3:24][C:25]1[CH:29]=[C:28]([NH2:30])[S:27][N:26]=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:21]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C@@H:9]2[CH2:15][CH2:14][CH2:13][CH2:12][N:11]([C:16]([N:18]([CH3:20])[CH3:19])=[O:17])[CH2:10]2)=[N:7][C:2]=1[NH:30][C:28]1[S:27][N:26]=[C:25]([CH3:24])[CH:29]=1)#[N:22]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 27239183-Methylisothiazol-5-ylamine hydrochlorideHCID 118115233HCID 118115233, compound

Product 1

HCID 118114929HCID 118114929, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
115 °C

Procedure

(R)-3-(6-Chloro-5-cyanopyrazin-2-ylamino)-N,N-dimethylazepane-1-carboxamide (509) (53 mg, 0.16 mmol) was combined with 3-methylisothiazol-5-amine hydrochloride (45 mg, 0.39 mmol), Pd(OAc)2 (14 mg, 0.062 mmol), BINAP (36 mg, 0.058 mmol), and Cs2CO3 (196 mg, 0.601 mmol). The solids were suspended in dioxane (10 mL degassed for 10 minutes with Nitrogen sparge) and the resulting suspension was stirred at 115° C. for 4 hours. The reaction mixture was cooled to RT, filtered, and purified by prep-TLC (EtOAc/DCM) to give (R)-3-(5-cyano-6-(3-methylisothiazol-5-ylamino)pyrazin-2-ylamino)-N,N-dimethylazepane-1-carboxamide (510) (20 mg, 0.050 mmol, 31% yield).

Workup

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered
  3. custompurified by prep-TLC (EtOAc/DCM)

Sources & evidence

ORD record
ord-21f3c8f3ffd549beabe516d1d4c5809f
Source dataset
uspto-grants-2016_07
Patent number
US09382246B2

Reaction notes

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