HCID 86753660, compound → HCID 178496046, compound

HRID 361726Notes

Reaction equation

HRID 361726 reaction equation
[CH3:1][O:2][CH2:3][C:4]([NH:6][CH2:7][C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[CH2:11][NH:12]C(=O)OC(C)(C)C)=[NH:5].C(=O)(OCC1C=CC=C(CN)C=1)N>FC(F)(F)C(O)=O>[NH2:12][CH2:11][C:10]1[CH:9]=[C:8]([CH:22]=[CH:21][CH:20]=1)[CH2:7][NH:6][C:4](=[NH:5])[CH2:3][O:2][CH3:1]

Participants

4

Reactant 2

HCID 86753660HCID 86753660, compoundHCID 178496047HCID 178496047, compound

Product 1

HCID 178496046HCID 178496046, compoundYield 61.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The intermediate tert-butyl N-(3-((2-methoxyacetimidoyl) aminomethyl)benzyl)-carbamate (360 mg) prepared from tert-butyl N-(3-(aminomethyl)benzyl carbamate and intermediate G analogous to example 1 was deprotected in trifluoroacetic acid at 20° C. for 16 h. The crude product was purified by C18 reverse phase chromatography eluting with water (0.1% trifluoroacetic acid) to yield 150 mg of N-(3-(Aminomethyl)benzyl)-2-methoxyacetamidine as a yellowed, viscous oil (freeze-dried). Mass spectrum (CI) 208.0 (MH+, 100%). 1H NMR (200 MHz, D2O) δ 7.5-7.3 (m, 4H), 4.57 (s, 2H), 4.37 (s, 2H), 4.15 (s, 2H), 3.44 (s, 3H).

Workup

  1. customThe crude product was purified by C18 reverse phase chromatography
  2. washeluting with water (0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-b65a10613f9449ea8497d427e2c0a0bf
Source dataset
uspto-grants-1999_02
Patent number
US05866612

Reaction notes

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