Hydrochloric Acid → HCID 178423291, compound

HRID 1371140Notes

Reaction equation

HRID 1371140 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:24]=[C:12]3[NH:13][C:14]([CH:17]4[CH2:22][CH2:21][NH:20][CH:19]([CH3:23])[CH2:18]4)=[N:15][CH:16]=[C:11]3[N:10]=2)=[CH:5][CH:4]=1.B(Br)(Br)Br.CCN(CC)CC.[ClH:36]>C(Cl)Cl.C(Cl)(Cl)Cl>[OH2:2].[ClH:36].[CH3:23][CH:19]1[CH2:18][CH:17]([C:14]2[NH:13][C:12]3=[CH:24][C:9]([C:6]4[CH:5]=[CH:4][C:3]([OH:2])=[CH:8][CH:7]=4)=[N:10][C:11]3=[CH:16][N:15]=2)[CH2:22][CH2:21][NH:20]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 25134Boron tribromideHCID 178488442HCID 178488442, compound

Product 1

HCID 178423291HCID 178423291, compoundYield 32%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-70 °C

Procedure

The suspension of 4-methoxy-1-(2-methyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl)benzene (Example 71(e)) (0.138 g, 0.43 mmol) in anhydrous CH2Cl2 (12 mL) was cooled to −70° C. under nitrogen atmosphere. Boron tribromide (Aldrich Chemical Company) (0.41 mL, 4.3 mmol) in CH2Cl2 (4 mL) was added dropwise. The reaction mixture was stirred at −70° C. to room temperature for 16 h. The solution was poured into 40 mL of ice-water. The resulting mixture was basified with Et3N to pH 10 and stirred for a period of 3 h. The precipitate that formed was collected by filtration, washed with H2O, and dried in a vacuum oven to give 78.7 mg (60%),of a tan solid. A portion of this material (74 mg, 0.24 mmol) was dissolved in minimum amount of CHCl3 and ethereal hydrogen chloride (1N, 0.26 mL, 0.26 mmol) was added dropwise. The mixture was stirred at room temperature for 20 min. Solvent was then evaporated in vacuo to give a brown solid, which was recrystallized from MeOH/H2O to give 25 mg of the title compound as light-tan crystals. MP:>300° C. (dec). 1H NMR (DMSO-d6; 400 MHz): δ 1.70 (m, 6), 2.55 (s, 3), 4.03 (m, 4), 6.73 (s, 1), 6.93 (d, 2, J=8.54), 7.79 (d, 2, J=8.54), 10.04 (s, 1), 11.75 (br s, 1), 14.15 (br s, 1); MS m/z: 309 (M+1), 307 (M−1). Calcd for C18H21ClN4OH2O: C, 59.58; H, 6.39; N, 15.44. Found: C, 59.13; H, 6.33; N, 15.20.

Workup

  1. stirringstirred for a period of 3 h
  2. customThe precipitate that formed
  3. filtrationwas collected by filtration
  4. washwashed with H2O
  5. customdried in a vacuum oven
  6. customto give 78.7 mg (60%)
  7. additionwas added dropwise
  8. stirringThe mixture was stirred at room temperature for 20 min
  9. customSolvent was then evaporated in vacuo
  10. customto give a brown solid, which
  11. customwas recrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-095bf6992cc949ea96560cbeda58afa0
Source dataset
uspto-grants-2003_06
Patent number
US06583154B1

Reaction notes

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