Hydrochloric Acid → HCID 178423309, compound

HRID 1371159Notes

Reaction equation

HRID 1371159 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[NH:13][CH:12]([CH3:14])[CH2:11][CH:10]([C:15]2[NH:20][C:19]3=[CH:21][CH:22]=[N:23][C:18]3=[CH:17][N:16]=2)[CH2:9]1.CC[O:26]C(C)=O.[ClH:30]>CO>[OH2:26].[ClH:30].[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]1[NH:13][CH:12]([CH3:14])[CH2:11][CH:10]([C:15]2[NH:20][C:19]3=[CH:21][CH:22]=[N:23][C:18]3=[CH:17][N:16]=2)[CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 178423308HCID 178423308, compound

Product 1

HCID 178423309HCID 178423309, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Using the method described in Example 30 by employing [1-(2-fluorophenyl)vinyl]pyrrolidine (freshly prepared before use) (1.02 g, 5.34 mmol), 2-methyl-4,6-dichloro-5-nitropyrimidine (Example 76(b)) (1.10 g, 5.34 mmol), N,N-diisopropylethyl amine (Aldrich Chemical Company) (1.3 mL, 7.73 mmol), piperidine (Aldrich Chemical Company) (0.9 mL, 5.34 mmol), NEt3 (Aldrich Chemical Company) (1.0 mL) and SnCl2 (Aldrich Chemical Company) (16 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 142 mg (9%) of the free base as a cream colored solid. 1H NMR (DMSO-d6; 400 MHz): δ 1.65 (br s, 6), 2.43 (s, 3), 3.73 (br s, 4), 6.63 (s, 1), 7.33 (br s, 3), 7.44 (br s, 1), 7.87 (s, 1), 11.04 (s, 1). MS m/z: 311 (M+1). To a hot solution of 6-(2-fluorophenyl)-2-methyl-4-piperidylpyrrolo[3,2-d]pyrimidine (0.14 g, 0.46 mmol) in 5:1 EtOAc:MeOH (30 mL) was added 1N etheral HCl (Aldrich Chemical Company) (460 mL, 0.46 mmol). Crystallization occurred as the mixture cooled and the precipitate was collected by filtration, washed with Et2O (3×10 mL) and dried under vacuum to give 140 mg (88%) of the title compound as white colored long needles. Mp: 287-289° C. 1H NMR (DMSO-d6; 400 MHz): δ 1.72 (br s, 6), 2.58 (s, 3), 4.05 (br s, 4), 6.80 (d, 1, J=1.6), 7.39-7.46 (m, 2), 7.57 (q, 1, J=7.1), 7.89 (t, 1, J=7.7), 12.13 (s, 1), 14.37 (s, 1). MS m/z: 311 (M+1). Anal. Calcd for C18H19FN4.HCl.H2O: C, 59.28; H, 6.08; N, 15.37; Cl, 9.72. Found C, 59.28; H, 6.02; N, 15.39; Cl, 9.77.

Workup

  1. customCrystallization
  2. temperaturecooled
  3. filtrationthe precipitate was collected by filtration
  4. washwashed with Et2O (3×10 mL)
  5. customdried under vacuum

Sources & evidence

ORD record
ord-ee3cca479c074de28947984b61f857f6
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

Loading…