Hydrochloric Acid → HCID 178423276, compound

HRID 1371148Notes

Reaction equation

HRID 1371148 reaction equation
[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[CH:14][C:15]([C:17]4[O:21][C:20]5[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=5[CH:18]=4)=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH2:4][NH:3]1.CCOC(C)=O.[ClH:32]>CO>[OH2:21].[ClH:32].[CH3:1][CH:2]1[CH2:7][CH:6]([C:8]2[NH:13][C:12]3=[CH:14][C:15]([C:17]4[O:21][C:20]5[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=5[CH:18]=4)=[N:16][C:11]3=[CH:10][N:9]=2)[CH2:5][CH2:4][NH:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178423275HCID 178423275, compound

Product 1

HCID 178423276HCID 178423276, compoundYield 179.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing 2-(1-pyrrolidinylvinyl)benzo[b]furan (freshly prepared before use) (2.21 g, 10.4 mmol), 2-ethyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (2.10 g, 10.4 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (1.8 mL, 10.4 mmol), piperidine (Aldrich Chemical Company) (1.6 mL, 16.6 mmol), NEt3 (Aldrich Chemical Company) (2.0 mL) and SnCl2 (31 mL of a 2M solution in DMF). The residue was purified by flash chromatography on silica gel with 95:5 CHCl3:MeOH as elutant to give 560 mg (16%) of the free base as a beige colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.67 (s, 6), 2.44 (s, 3), 3.30 (s, 2, under H2O), 3.74 (s, 2), 6.83 (m, 1), 7.28 (br s, 3), 8.77 (br s, 2), 11.36 (s, 1). MS m/z: 333 (M+1). To a hot solution of 2-(2-methyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl)benzo[b]furan (Example 85(a)) (0.56 g, 1.69 mmol) in 5:1 EtOAc:MeOH (30 mL) was added 1M etheral HCl (Aldrich Chemical Company) (1.70 mL, 1.69 mmol). Upon cooling crystalliztion occurred and the solid was collected by filtration. This material was washed with Et2O (2×10 mL) and dried under vacuum to give 588 mg (95%) of the title compound as a beige colored solid. Mp:>280° C. 1H NMR (DMSO-d6; 400 MHz) δ 1.73 (s, 6), 2.58 (s, 3), 4.08 (s, 4), 7.00 (s, 1), 7.35 (t, 1, J=7.5), 7.44 (t, 1, J=8.0), 7.71 (d, 1, J=8.2), 7.79 (d, 1, J=7.7), 7.88 (s, 1), 12.48 (s, 1), 14.40 (s, 1). MS m/z: 333 (M+1). Anal. Calcd for C20H20N4O.HCl.H2O: C, 62.25; H, 5.71; N, 14.52; Cl, 9.19. Found C, 62.22; H, 5.94; N, 14.54; Cl, 9.22.

Workup

  1. temperatureUpon cooling crystalliztion
  2. filtrationthe solid was collected by filtration
  3. washThis material was washed with Et2O (2×10 mL)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-668e3f298d084ae1a21e144bcf41e160
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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