Methanol → HCID 67002131, compound

HRID 2279227Notes

Reaction equation

HRID 2279227 reaction equation
[CH2:1]([N:8]1[CH2:22][CH2:21][N:11]2[C:12]3[N:20]=[CH:19][CH:18]=[CH:17][C:13]=3[NH:14][CH2:15][CH2:16][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31](Cl)=[O:32])=[CH:26][CH:25]=1.CO>C(Cl)Cl>[CH2:1]([N:8]1[CH2:22][CH2:21][N:11]2[C:12]3[N:20]=[CH:19][CH:18]=[CH:17][C:13]=3[N:14]([C:31](=[O:32])[CH2:30][C:27]3[CH:28]=[CH:29][C:24]([Cl:23])=[CH:25][CH:26]=3)[CH2:15][CH2:16][CH:10]2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 906924-Chlorophenylacetyl chlorideHCID 54670219HCID 54670219, compound

Product 1

HCID 67002131HCID 67002131, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the product of Example 52 (135 mg, 0.367 mmol) in CH2Cl2 (3 mL) was added to 4-chlorophenylacetyl chloride (Aldrich, 0.058 mL, 0.38 mmol), and the resulting solution was stirred at room temperature for 45 minutes. Methanol (0.5 mL) was added and the mixture was stirred for 10 minutes and then concentrated under vacuum. The residue was crystallized from ethanol (4 mL) and water (0.2 mL) to provide the title compound as the HCl salt: 1H NMR (400 MHz, pyridine-d5) δ ppm 2.57-2.86 (m, 3H), 2.92-3.31 (m, 2H), 3.32-3.59 (m, 7H), 4.29-4.66 (m, 2H), 6.69-6.88 (m, 1H), 6.91-7.04 (m, 2H), 7.21 (d, J=8.2 Hz, 2H), 7.25 (d, J=7.3 Hz, 1H), 7.27-7.36 (m, J=7.3, 7.3 Hz, 3H), 7.37-7.44 (m, 2H), 8.23-8.33 (m, 1H), one proton obscured by solvent; MS (ESI) m/z 447/449 (M+H)+. Elemental analysis is calculated for C26H27N4OCl.HCl.0.4H2O: C, 63.65; H, 5.92; N, 11.42. Found: C, 63.72; H, 5.75; N, 11.26.

Workup

  1. stirringthe mixture was stirred for 10 minutes
  2. concentrationconcentrated under vacuum
  3. customThe residue was crystallized from ethanol (4 mL) and water (0.2 mL)

Sources & evidence

ORD record
ord-cf8cb7e70adf47f9890af6e0ea8d39a1
Source dataset
uspto-grants-2015_09
Patent number
US09133206B2

Reaction notes

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