Hydrochloric Acid → HCID 178505456, compound

HRID 243514Notes

Reaction equation

HRID 243514 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][NH:11][C:12]3[N:20]=[CH:19][N:18]=[C:17]4[C:13]=3[N:14]=[CH:15][N:16]4C3CCCCO3)[N:7]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:6]=2[CH:33]=1.Cl>CO.O1CCOCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[C:8]([CH2:10][NH:11][C:12]3[N:20]=[CH:19][N:18]=[C:17]4[C:13]=3[N:14]=[CH:15][NH:16]4)[N:7]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:6]=2[CH:33]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 68157269HCID 68157269, compound

Product 1

HCID 178505456HCID 178505456, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

(6-Fluoro-1-phenyl-1H-benzoimidazol-2-ylmethyl)[9-(tetrahydropyran-2-yl)-9H-purin-6-yl]amine (0.125 g, 0.28 mmol) in MeOH (2 mL) was treated with 4M HCl in dioxane (0.35 mL). After 15 min at 20° C. the reaction was poured onto a 10 g SCX cartridge which was eluted first with methanol then with 1:1 MeOH/2M NH3 in isopropanol. Product containing fractions were evaporated to a white solid. This was triturated with diethyl ether and dried to give 443 as a white solid, (86 mg, 85%). LCMS (Method C): RT 3.16 min [M+H]+ 360.02. NMR δ (ppm) (DMSO-d6): 12.9 (1H, s), 8.11 (2H, s), 7.92 (1H, s), 7.66-7.60 (6H, m), 7.09 (1H, td, J=9.31, 2.45 Hz), 6.93 (1H, dd, J=8.96, 2.50 Hz), 4.8 (2H, bs)

Workup

  1. additionAfter 15 min at 20° C. the reaction was poured onto a 10 g SCX cartridge which
  2. washwas eluted first with methanol
  3. additionProduct containing fractions
  4. customwere evaporated to a white solid
  5. customThis was triturated with diethyl ether
  6. customdried

Sources & evidence

ORD record
ord-25495d19e9ff47ce97b4990df5f33098
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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