Trifluoroacetic acid → HCID 90460435, compound

HRID 2202095Notes

Reaction equation

HRID 2202095 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([CH2:14][N:15]([CH3:26])[CH2:16][CH2:17][NH:18]C(=O)OC(C)(C)C)=[CH:12][CH:11]=[N:10]2)=[CH:5][CH:4]=1)#[N:2].[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30]>ClCCl>[F:27][C:28]([F:33])([F:32])[C:29]([OH:31])=[O:30].[NH2:18][CH2:17][CH2:16][N:15]([CH2:14][C:13]1[N:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)[N:10]=[CH:11][CH:12]=1)[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90463183HCID 90463183, compound

Product 1

HCID 90460435HCID 90460435, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl N-[2-([[1-(4-cyanophenyl)-1H-pyrazol-5-yl]methyl](methyl)amino)ethyl]carbamate (100 mg, 0.28 mmol, 1.00 equiv) in dichloromethane (5 mL) and trifluoroacetic acid (3 mL) was stirred at 25° C. for 30 min. The resulting mixture was concentrated under vacuum to give 196.2 mg (85%) of 4-(5-(((2-aminoethyl)(methyl)amino)methyl)-1H-pyrazol-1-yl)benzonitrile trifluoroacetate as a colorless oil. 1H-NMR (300 MHz, D2O): δ 7.94-7.91 (m, 2H), 7.80 (d, J=2.7 Hz, 1H), 7.61-7.58 (m, 2H), 6.78 (d, J=1.8 Hz, 1H), 4.52 (s, 2H), 3.30-3.18 (m, 4H), 2.57 (s, 3H) ppm. LCMS (method R, ESI): RT=1.18 min, m/z=256.1 [M+H]+.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-3e6e46055d0a49a6a7ea9aa12e25a06a
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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