Trifluoroacetic acid → HCID 135517369, compound

HRID 2268182Notes

Reaction equation

HRID 2268182 reaction equation
CC(O[C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]2[C:20]3[CH:21]=[CH:22][C:23]4[NH:27][C:26](=[O:28])[CH2:25][C:24]=4[C:19]=3[O:18][N:17]=2)[CH2:10][CH2:9]1)=O)(C)C.C(O)(C(F)(F)F)=O.C([O-])([O-])=O.[Na+].[Na+].C(Br)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C(Cl)Cl.CN(C=O)C>[C:43]1([CH2:6][N:8]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][C:16]3[C:20]4[CH:21]=[CH:22][C:23]5[NH:27][C:26](=[O:28])[CH2:25][C:24]=5[C:19]=4[O:18][N:17]=3)[CH2:10][CH2:9]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 7498Benzyl BromideHCID 10340Sodium CarbonateHCID 135457451HCID 135457451, compound

Product 1

HCID 135517369HCID 135517369, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The procedure described in Example 12f was followed with the piperidine obtained in step e (0.042 g, 0.109 mmol) and TFA (1.5 mL) in CH2Cl2 (6 mL), Na2CO3 (0.058 g, 0.545 mmol) and benzyl bromide (0.016 mL, 0.131 mmol) in DMF (6 mL). After purification by chromatography (1-10% MeOH—CH2Cl2), the title compound (0.018 g, 44%) was obtained as an off-white solid.

Workup

  1. customAfter purification by chromatography (1-10% MeOH—CH2Cl2)

Sources & evidence

ORD record
ord-97855e9cbc80478195b29aa14e3bada5
Source dataset
uspto-grants-2001_12
Patent number
US06326382B1

Reaction notes

Loading…