Hydrochloric Acid → HCID 178433098, compound

HRID 1371229Notes

Reaction equation

HRID 1371229 reaction equation
[CH3:1][C:2]1[NH:7][C:6]2=[CH:8][C:9]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[N:10][C:5]2=[C:4]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:3]=1.CCN(CC)CC.[CH3:30][S:31]([Cl:34])(=[O:33])=[O:32].Cl>C1COCC1.CCOC(C)=O>[OH2:32].[ClH:34].[CH3:1][C:2]1[NH:7][C:6]2[C:5]([N:10]=[C:9]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:8]=2)=[C:4]([N:17]2[CH2:22][CH2:21][N:20]([S:31]([CH3:30])(=[O:33])=[O:32])[CH2:19][CH2:18]2)[N:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 178433086HCID 178433086, compound

Product 1

HCID 178433098HCID 178433098, compoundYield 144%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
0 °C

Procedure

To an oven-dried, 50-mL, round-bottomed flask was added 2-methyl-6-phenyl-4-piperazinylpyrrolo[3,2-d]pyrimidine (Example 26) (400 mg, 1.36 mmol) was suspended in anhydrous THF (20 mL) and Et3N (0.4 mL, 2.8 mmol) was added. The mixture was cooled to 0° C. and methanesulfonyl chloride (Aldrich Chemical Company) (0.12 mL, 1.5 mmol) was added dropwise and allowed to warm to room temperature over 30 min. EtOAc (50 mL) was added to the mixture which was extracted with saturated NaHCO3 (3×50 mL). The organic layer was washed with saturated NaCl (75 mL), dried over MgSO4, filtered and evaporated in vacuo to give 450 mg (89% yield) as a light yellow solid. The free base (440 mg, 1.2 mmol) was dissolved in hot EtOAc (20 mL) and anhydrous ethereal HCl (1.18 mL, of a 1.0 M soln, 1.18 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 460 mg (95.6% yield) of the title compound as a light yellow solid. Mp: 280-282° C. 1H NMR (DMSO-d6; 400 MHz); d 2.54 (s, 3), 2.88 (s, 3), 3.29 (s, 4), 4.13 (t, 4, J=4.62), 6.9 (s, 1), 7.51 (m, 3), 7.94 (d, 2, J=6.85). MS m/z: 372 (M+1); 370 (M−1). Anal. Calcd for C18H21N5O2S.HCl.H2O.: C, 50.46; H, 5.70; N, 16.35; Cl, 8.41. Found: C, 50.71; H, 5.60; N, 16.22; Cl, 8.45.

Workup

  1. temperatureto warm to room temperature over 30 min
  2. extractionwas extracted with saturated NaHCO3 (3×50 mL)
  3. washThe organic layer was washed with saturated NaCl (75 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give 450 mg (89% yield) as a light yellow solid
  8. temperatureto cool to room temperature
  9. filtrationThe resulting solid was filtered
  10. customdried under high vacuum

Sources & evidence

ORD record
ord-37fe02c06b694f5999ec27b7be291b47
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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