Hydrochloric Acid → HCID 24901139, compound

HRID 1158749Notes

Reaction equation

HRID 1158749 reaction equation
Cl.[NH2:2][C:3]1[C:4]([C:28]([NH2:30])=[O:29])=[CH:5][C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:15][C@@H:16]([NH2:26])[CH2:17][O:18]CC3C=CC=CC=3)[C:7]=2[N:27]=1.I[Si](C)(C)C.Cl>C(Cl)(Cl)Cl.CO>[NH2:2][C:3]1[C:4]([C:28]([NH2:30])=[O:29])=[CH:5][C:6]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:15][C@@H:16]([NH2:26])[CH2:17][OH:18])[C:7]=2[N:27]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 85247Trimethylsilyl iodideHCID 66676248HCID 66676248, compound

Product 1

HCID 24901139HCID 24901139, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a cooled (0° C.) solution of 2-amino-9-[(2R)-2-amino-3-(benzyloxy)propyl]-9H-pyrido[2,3-b]indole-3-carboxamide (61, 81 mg, 0.160 mmol) in chloroform (2 mL) was added iodotrimethylsilane (140 uL, 0.990 mmol). The reaction was stirred under argon, allowed to warm slowly to room temperature and then stirred an additional 16 h. The reaction mixture was filtered and concentrated in vacuo. The crude mixture was purified by reverse phase HPLC (Phenomenex Luna 15 μm C18, aqueous NH4OAc/CH3CN) to provide the product which was then converted to the hydrochloride salt by stirring with a solution of excess hydrochloric acid in methanol to afford 2-amino-9-[(2R)-2-amino-3-hydroxypropyl]-9H-pyrido[2,3-b]indole-3-carboxamide (65, 24 mg, 45%). NH4OAc standard conditions. DAD Retention time =4.76 min. M+H=300. 1H NMR (300 MHz, MeOD-d4): Δ 8.97 (s, 1H), 8.01 (d, J=7.0 Hz, 1H) 7.67 (d, J=7.4 Hz, 1H), 7.52 (t, J=6.9, 1H), 7.38 (t, J=6.9 Hz, 1H), 4.75-4.69 (m, 2H), 3.96-3.81 (m, 2H), 3.71-3.62 (m, 1H).

Workup

  1. stirringstirred an additional 16 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated in vacuo
  4. customThe crude mixture was purified by reverse phase HPLC (Phenomenex Luna 15 μm C18, aqueous NH4OAc/CH3CN)
  5. customto provide the product which

Sources & evidence

ORD record
ord-5c79ada582724329919a07596a550d15
Source dataset
uspto-grants-2010_10
Patent number
US07812018B2

Reaction notes

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