Cesium carbonate → 4-[4-((1R,2R)-1-acetylamino-indan-2-yloxy)-5-trifluoromethyl-pyrimidin-2-ylamino]-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide

HRID 1258174Notes

Reaction equation

HRID 1258174 reaction equation
[OH:1][C@@H:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C@H:3]1[NH:11][C:12](=[O:14])[CH3:13].Cl[C:16]1[C:21]([C:22]([F:25])([F:24])[F:23])=[CH:20][N:19]=[C:18]([NH:26][C:27]2[CH:42]=[CH:41][C:30]([C:31]([NH:33][CH:34]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]3)=[O:32])=[CH:29][C:28]=2[O:43][CH3:44])[N:17]=1.C([O-])([O-])=O.[Cs+].[Cs+].[O-]S([O-])(=O)=O.[Mg+2]>O1CCOCC1>[C:12]([NH:11][C@@H:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:10][C@H:2]1[O:1][C:20]1[C:21]([C:22]([F:23])([F:25])[F:24])=[CH:16][N:17]=[C:18]([NH:26][C:27]2[CH:42]=[CH:41][C:30]([C:31]([NH:33][CH:34]3[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]3)=[O:32])=[CH:29][C:28]=2[O:43][CH3:44])[N:19]=1)(=[O:14])[CH3:13]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 15760043trans-1-Acetamido-2-indanolHCID 582009164-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide

Product 1

HCID 584508914-[4-((1R,2R)-1-acetylamino-indan-2-yloxy)-5-trifluoromethyl-pyrimidin-2-ylamino]-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-((1R,2R)-2-hydroxy-indan-1-yl)-acetamide (43 mg) and 4-(4-chloro-5-trifluoromethyl-pyrimidin-2-ylamino)-3-methoxy-N-(1-methyl-piperidin-4-yl)-benzamide (50 mg) are suspended in 0.70 mL dioxane, mixed with Cs2CO3 (184 mg) and some MgSO4 and stirred overnight at 85° C. The reaction mixture is allowed to cool to RT and the solvent is eliminated using the rotary evaporator. The residue is taken up in MeOH and purified by preparative HPLC. The product-containing fractions are freeze-dried.

Workup

  1. customthe rotary evaporator
  2. custompurified by preparative HPLC
  3. customThe product-containing fractions are freeze-dried

Sources & evidence

ORD record
ord-d380c514ca2b4184b428b80d2e8d96ca
Source dataset
uspto-grants-2013_06
Patent number
US08466155B2

Reaction notes

Loading…