HCID 71466164, compound → HCID 71466234, compound

HRID 572672Notes

Reaction equation

HRID 572672 reaction equation
Cl.[F:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[C:15]([C:17]3[CH2:21][CH:20]([CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[O:19][N:18]=3)[N:14]=[C:13]([CH3:28])[N:12]=2)=[O:10])=[CH:5][C:4]=1[O:31][CH3:32].F[C:34](C1C(F)=C(F)C(F)=C(F)C=1F)([S:38]([C:41](F)(F)F)(=[O:40])=[O:39])[C:35]([O-])=[O:36]>C(Cl)Cl>[F:2][C:3]1[CH:30]=[CH:29][C:6]([CH2:7][NH:8][C:9]([C:11]2[CH:16]=[C:15]([C:17]3[CH2:21][CH:20]([CH:22]4[CH2:23][CH2:24][N:25]([C:35](=[O:36])[CH2:34][S:38]([CH3:41])(=[O:40])=[O:39])[CH2:26][CH2:27]4)[O:19][N:18]=3)[N:14]=[C:13]([CH3:28])[N:12]=2)=[O:10])=[CH:5][C:4]=1[O:31][CH3:32]

Participants

4

Reactant 2

HCID 71466164HCID 71466164, compoundHCID 131732829HCID 131732829, compound

Product 1

HCID 71466234HCID 71466234, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N-(4-fluoro-3-methoxybenzyl)-2-methyl-6-(5-(piperidin-4-yl)-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxamide hydrochloride (0.20 g, 0.43 mmol Preparation #K. 1) in DCM (10 mL) was added TEA (0.13 g, 1.29 mmol, Spectrochem) and perfluorophenyl-2-(methylsulfonyl)acetate (0.196 g, 0.645 mmol, See Ref: US 20090312338). The resulting solution was stirred at RT for about 16 h. The crude reaction mixture was purified by preparative HPLC (Table 2, Method f) to afford N-(4-fluoro-3-methoxybenzyl)-2-methyl-6-(5-(1-(2-(methylsulfonyl)acetyl)piperidin-4-yl)-4,5-dihydroisoxazol-3-yl)pyrimidine-4-carboxamide 0.072 g (31.3%); LC/MS (Table 1, Method d) Rt=0.55 min; MS m/z: 548.3 (M+H)+.

Workup

  1. customThe crude reaction mixture
  2. customwas purified by preparative HPLC (Table 2, Method f)

Sources & evidence

ORD record
ord-dd8024c35e02426db212815a9026cbdf
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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