Acetonitrile--hydrogen chloride (1/1) → HCID 178425348, compound

HRID 1987053Notes

Reaction equation

HRID 1987053 reaction equation
[C:1]([NH:4][O:5][CH2:6][CH2:7][NH:8][C:9](=[O:32])[CH2:10][C:11]1[C:16]([C:17]#[N:18])=[CH:15][CH:14]=[C:13]([NH:19][CH2:20][C:21]([F:30])([F:29])[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=2)[C:12]=1[F:31])(=[NH:3])[NH2:2].[ClH:33].CC#N>CC#N>[ClH:33].[C:1]([NH:4][O:5][CH2:6][CH2:7][NH:8][C:9](=[O:32])[CH2:10][C:11]1[C:16]([C:17]#[N:18])=[CH:15][CH:14]=[C:13]([NH:19][CH2:20][C:21]([F:29])([F:30])[C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][N:23]=2)[C:12]=1[F:31])(=[NH:2])[NH2:3]

Participants

4

Reactant 2

HCID 22261314Acetonitrile--hydrogen chloride (1/1)HCID 178425347HCID 178425347, compound

Product 1

HCID 178425348HCID 178425348, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of N-[2-(Amidinoaminooxy)ethyl]-2-{3-[(2,2-difluoro-2-(5-methylpyridyl)ethyl)amino]-6-cyano-2-fluorophenyl}acetamide (1.01 g, 2.24 mmol), as prepared in the previous step, dissolved into CH3CN (25 mL) was treated with 2.0 mL, 2.425 M HCl/CH3CN. The product (900 mg) was collected by filtration and recrystallized from EtOAc/MeOH to afford the final product as a pale yellow solid (800 mg, 1.65 mmol, 74% yield). 1H NMR (300 Hz, CDCl3) δ 8.51 (s, 1H), 7.78-7.76 (m, 1H), 7.60 (d, J=8.0 Hz, 1H), 7.31-7.28 (m, 1H), 6.85 (t, J=8.6 Hz, 1H); 4.10 (t, J=14.2 Hz, 2H), 3.94 (t, J=5.3 Hz, 2H), 3.75 (d, J=1.65, 2H), 3.51 (t, J=5.6 Hz, 2H), 2.42 (s, 3H); LC/MS (m/z) [M+1]+ 450.2 (calculated for C20H23F3N7O2, 450.4). Elem. Anal. Calc. for free base •1.1 HCl•0.22H2O: C, 48.35; H, 4.73; N, 19.73. Found: C, 48.44; H, 4.47; N, 19.61; Cl, 7.95. Karl Fischer % water: 0.86.

Workup

  1. filtrationThe product (900 mg) was collected by filtration
  2. customrecrystallized from EtOAc/MeOH

Sources & evidence

ORD record
ord-bd11647cfc724739a0afeee8bca95394
Source dataset
uspto-grants-2009_06
Patent number
US07550474B2

Reaction notes

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