N-Benzyl-N',N'-dimethyl-N-[3-(1-trityl-1H-benzotriazol-5-yl)-benzyl]-propane-1,3-diamine → HCID 178483525, compound

HRID 1864774Notes

Reaction equation

HRID 1864774 reaction equation
[CH2:1]([N:8]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([C:22]2[CH:49]=[CH:48][C:25]3[N:26](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[N:27]=[N:28][C:24]=3[CH:23]=2)[CH:17]=1)[CH2:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.O1CCOCC1.Cl>[NH:26]1[C:25]2[CH:48]=[CH:49][C:22]([C:18]3[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=3)[CH2:15][N:8]([CH2:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:9][CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])=[CH:23][C:24]=2[N:28]=[N:27]1

Participants

5

Reactant 1

HCID 68748346N-Benzyl-N',N'-dimethyl-N-[3-(1-trityl-1H-benzotriazol-5-yl)-benzyl]-propane-1,3-diamine

Product 1

HCID 178483525HCID 178483525, compoundYield 80.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolvent2×HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

N-Benzyl-N′,N′-dimethyl-N-[3-(1-trityl-1H-benzotriazol-5-yl)-benzyl]-propane-1,3-diamine (60 mg, 0.093 mmol) was dissolved in a mixture of 5 mL of ethanol, 5 mL of dioxane and 8 mL of 2M aqueous hydrochloric acid solution, and the resulting mixture was stirred at room temperature for 6 h. The volatiles were removed in vacuo and the residue partitioned between diethyl ether and 1M HCl solution. The aqueous phase was washed with diethyl ether and the combined organic phases were concentrated in vacuo to obtain the crude product, which was dissolved in small amount of 1M HCl solution and freeze dried. Purification by HPLC (elution with 30% acetonitrile/70% water (containing 0.1% trifluoroacetic acid)) afforded 30 mg of the title compound. LC/MS (short method): Retention time 1.19 min; (M+H)=400.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue partitioned between diethyl ether and 1M HCl solution
  3. washThe aqueous phase was washed with diethyl ether
  4. concentrationthe combined organic phases were concentrated in vacuo
  5. customto obtain the crude product, which
  6. customdried
  7. customPurification
  8. washby HPLC (elution with 30% acetonitrile/70% water (containing 0.1% trifluoroacetic acid))

Sources & evidence

ORD record
ord-cc4b61e2ee1e4f9495334605dcf1629c
Source dataset
uspto-grants-2009_12
Patent number
US07625889B2

Reaction notes

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