Hydrochloric Acid → HCID 178511547, compound

HRID 1819470Notes

Reaction equation

HRID 1819470 reaction equation
C(OC(=O)[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:25][CH2:26][C:27]3[C:28]([O:33]C)=[N:29][CH:30]=[CH:31][CH:32]=3)[N:17]=2)[CH2:10][CH2:9]1)(C)(C)C.Cl>O1CCOCC1>[NH2:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][NH:15][C:16]2[C:21]([N+:22]([O-:24])=[O:23])=[CH:20][N:19]=[C:18]([NH:25][CH2:26][C:27]3[C:28](=[O:33])[NH:29][CH:30]=[CH:31][CH:32]=3)[N:17]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178494115HCID 178494115, compound

Product 1

HCID 178511547HCID 178511547, compoundYield 26.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

[trans-4-({2-[(2-Methoxy-pyridin-3-ylmethyl)-amino]-5-nitro-pyrimidin-4-ylamino}-methyl)-cyclohexyl]-carbamic acid tert-butyl ester (100 mg, 0.205 mmol) was dissolved in dioxane (2 mL) and treated with HCl in dioxane (0.85 mL, 4 mmol/mL, 3.40 mmol). After stirring overnight, an oil was seen at the bottom of the solution. The solvent was taken out and the residue dried to give an oily solid. The crude solid was purified with prep TLC (1:9:90 NH3:MeOH:DCM) to give the title product (20.5 mg, 0.055 mmol, 26.8%) as a yellow solid, m/z 374.5 (M+1)+

Workup

  1. customthe residue dried
  2. customto give an oily solid
  3. customThe crude solid was purified with prep TLC (1:9:90 NH3:MeOH:DCM)

Sources & evidence

ORD record
ord-a35cf711ea7f4dff8d510a604831eda1
Source dataset
uspto-grants-2009_10
Patent number
US07601714B2

Reaction notes

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