Cesium carbonate → HCID 89450673, compound

HRID 2284045Notes

Reaction equation

HRID 2284045 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[CH2:9][CH3:10].[ClH:11].[N:12]1([CH2:16][CH2:17][N:18]2[CH:22]=[C:21](C3C=CN=C(C(F)(F)F)C=3)[N:20]=[C:19]2[CH:33]2[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH2:15][CH2:14][CH2:13]1.C([O-])([O-])=O.[Cs+].[Cs+]>CS(C)=O>[N:12]1([CH2:16][CH2:17][N:18]2[CH:22]=[C:21]([C:35]3[CH:34]=[CH:33][CH:38]=[C:37]([Cl:11])[N:36]=3)[N:20]=[C:19]2[CH:33]2[CH2:38][CH2:37][N:36]([C:2]3[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=3[CH2:9][CH3:10])[CH2:35][CH2:34]2)[CH2:13][CH2:14][CH2:15]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 58497086HCID 58497086, compoundHCID 89442760HCID 89442760, compound

Product 1

HCID 89450673HCID 89450673, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A reaction mixture of 6-Chloro-5-ethyl-pyrimidin-4-ylamine (45.00 mg; 0.29 mmol; 1.00 eq.), 2-[1-(2-Azetidin-1-yl-ethyl)-2-piperidin-4-yl-1H-imidazol-4-yl]-6-chloropyridine hydrochloride (4) (140.40 mg; 0.29 mmol; 1.00 eq.), and Cs2CO3 (372.13 mg; 1.14 mmol; 4.00 eq.) in DMSO 1.0 ml was stirred at 120° C. for 2 days, purified by HPLC, collected title compound 36 mg. LC-MS (M+1=467, obsd.=467).

Workup

  1. custompurified by HPLC
  2. customcollected title compound 36 mg

Sources & evidence

ORD record
ord-04d478a67d6f4b558c5107a55c94495c
Source dataset
uspto-grants-2015_09
Patent number
US09145392B2

Reaction notes

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