Trifluoroacetic acid → HCID 90461207, compound

HRID 2202113Notes

Reaction equation

HRID 2202113 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][N:11]=[CH: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)[CH:10]=[N:11][CH:12]=1)[CH3:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90463195HCID 90463195, compound

Product 1

HCID 90461207HCID 90461207, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl N-[2-([[1-(4-cyanophenyl)-1H-imidazol-5-yl]methyl](methyl)amino)ethyl]carbamate (90 mg, 0.25 mmol, 1.00 equiv) in trifluoroacetic acid (5 mL) and dichloromethane (5 mL) was stirred at room temperature for 3 h. The resulting mixture was concentrated under vacuum and the crude product was purified by Prep-HPLC with the following conditions (waters-1): Column, XBridge Shield RP18 OBD Column, 5 μm, 19×150 mm; mobile phase, Phase A: water with 0.03% NH4OH Phase B: water with 0.05% TFA; Gradient B (20%˜50% 2 min˜100% 11 min); Detector, UV 254 nm to afford 25.4 mg (39%) of 4-(5-(((2-aminoethyl)(methyl)amino)methyl)-1H-imidazol-1-yl)benzonitrile trifluoroacetate as a white solid. 1H-NMR (300 MHz, CD3OD): δ 7.98-7.95 (m, 3H), 7.83-7.80 (m, 2H), 7.15 (s, 1H), 3.60 (s, 2H), 2.76 (t, J=6.3 Hz, 2H), 2.50 (t, J=6.3 Hz, 2H), 2.16 (s, 3H) ppm. LCMS (method S, ESI): RT=1.18 min, m/z=256.3 [M+H]+.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum
  2. customthe crude product was purified by Prep-HPLC with the following conditions (waters-1)
  3. customGradient B (20%˜50% 2 min˜100% 11 min)

Sources & evidence

ORD record
ord-773af726096f4556bb4e20511575686d
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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