Hydrochloric Acid → HCID 178433094, compound

HRID 635764Notes

Reaction equation

HRID 635764 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH3:8])[NH:5][C:4]2=[CH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:3]=12.[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24].Cl>CCOC(C)=O>[OH2:18].[ClH:1].[O:18]1[CH:22]=[CH:21][CH:20]=[C:19]1[C:23]([N:25]1[CH2:26][CH2:27][N:28]([C:2]2[N:7]=[C:6]([CH3:8])[NH:5][C:4]3[C:3]=2[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=3)[CH2:29][CH2:30]1)=[O:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5502061-(2-Furoyl)piperazineHCID 178432852HCID 178432852, compound

Product 1

HCID 178433094HCID 178433094, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
180 °C

Procedure

To an oven-dried, 50-mL, round-bottomed flask was added 4-chloro-2-methyl-6-phenylpyrrolo[3,2-d]pyrimidine (Example 1(e)) (500 mg, 2.05 mmol) and the 1-(2-furoyl)piperazine (Avocado Chemical Company) (810 mg, 4.10 mmol). The flask was purged with N2 and the mixture was heated to 180° C. for 30 min. The reaction was allowed to cool to room temperature and the crude material was purified by flash chromatography on silica gel with 50% EtOAc/CHCl3 as eluant to give 500 mg (63% yield) of an off white solid. The free base (200 mg, 0.52 mmol) was dissolved in hot EtOAc (10 mL) and anhydrous ethereal HCl (0.52 mL, of a 1.0 M soln, 0.52 mmol) was added dropwise. The mixture was stirred for 2 h and allowed to cool to room temperature. The resulting solid was filtered and dried under high vacuum to give 205 mg (96% yield) of the title compound as a light yellow solid. Mp: 192-193° C. 1H NMR (DMSO-d6; 400 MHz): d 2.54 (s, 3), 3.89 (br s, 4), 4.17 (t, 4, J=4.3), 6.62 (q, 1, J=1.7), 6.9 (s, 1), 7.05 (d, 1, J=3.4), 7.4 (m, 3), 7.85 (s, 1), 7.93 (d, 2, J=6.92). MS m/z: 388 (M+1). Anal. Calcd for C22H21N5O2.HCl.H2O: C, 59.79; H, 5.47; N, 15.85; O, 10.86; Cl, 8.02. Found: C, 59.99; H, 5.33; N, 15.79; Cl, 8.06.

Workup

  1. customThe flask was purged with N2
  2. temperatureto cool to room temperature
  3. customthe crude material was purified by flash chromatography on silica gel with 50% EtOAc/CHCl3 as eluant
  4. customto give 500 mg (63% yield) of an off white solid
  5. temperatureto cool to room temperature
  6. filtrationThe resulting solid was filtered
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-36c3142eacb141ae8ef984e1bcbc5507
Source dataset
uspto-grants-2001_02
Patent number
US06187777B1

Reaction notes

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