Trifluoroacetic acid → 2-(Cyclopropylmethyl-amino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide

HRID 2080211Notes

Reaction equation

HRID 2080211 reaction equation
Cl[C:2]1[N:23]=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[S:9][C:10]([O:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:11][CH:12]=1)=[O:5].[NH2:24][CH2:25][CH:26]1[CH2:28][CH2:27]1.FC(F)(F)C(O)=O>CS(C)=O>[CH:26]1([CH2:25][NH:24][C:2]2[N:23]=[CH:22][CH:21]=[CH:20][C:3]=2[C:4]([NH:6][CH2:7][C:8]2[S:9][C:10]([O:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:11][CH:12]=2)=[O:5])[CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 75646CyclopropanemethanamineHCID 231303812-Chloro-N-[(5-phenoxythiophen-2-yl)methyl]pyridine-3-carboxamide

Product 1

HCID 231306992-(Cyclopropylmethyl-amino)-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamideYield 17%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-chloro-N-(5-phenoxy-thiophen-2-ylmethyl)-nicotinamide described in Preparation Example A+-7 (64 mg, 0.186 mmol) in dimethylsulfoxide (1 mL) was added (aminomethyl)cyclopropane (48 μl, 0.56 mmol), and the solution was stirred for 14 hours at 120° C. The reaction mixture was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used), and the title compound (15.6 mg, 0.0316 mmol, 17%) was obtained as a trifluoroacetic acid salt.

Workup

  1. customThe reaction mixture was purified by reverse phase high performance liquid chromatography (acetonitrile-water mobile phase (containing 0.1% trifluoroacetic acid) was used)

Sources & evidence

ORD record
ord-1871a22eed464dffaa3f3c78b6ad1fe4
Source dataset
uspto-grants-2011_04
Patent number
US07932272B2

Reaction notes

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