Benzamidine, hydrochloride → HCID 59129071, compound

HRID 2390502Notes

Reaction equation

HRID 2390502 reaction equation
[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[C:13]([N:14]=[C:15]=[S:16])=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:3])[CH3:2].C(N(C(C)C)CC)(C)C.Cl.[C:31]([NH2:39])(=[NH:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.CCOC(/N=N/C(OCC)=O)=O>CN(C=O)C>[C:1]([C:5]1[CH:20]=[CH:19][CH:18]=[CH:17][C:6]=1[O:7][C:8]1[C:13]([NH:14][C:15]2[S:16][N:39]=[C:31]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[N:38]=2)=[CH:12][CH:11]=[CH:10][N:9]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 80289Benzamidine, hydrochlorideHCID 81531DiisopropylethylamineHCID 5462977Diethyl azodicarboxylateHCID 59857388HCID 59857388, compound

Product 1

HCID 59129071HCID 59129071, compoundYield 78.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(2-tert-butylphenoxy)-3-isothiocyanatopyridine (Example 1a) (100 mg, 0.35 mmol), diisopropylethylamine (186 μL, 1.05 mmol) and benzamidine hydrochloride (55 mg, 0.35 mmol) in DMF (2 mL) was stirred at rt for 18 h. Diethylazodicarboxylate (110 μL, 0.7 mmol) was added and mixture was stirred for 4 h. The reaction mixture was purified by preparative HPLC to give the title compound (110 mg, TFA salt) as a white solid. (M+H)+=403. 1H NMR (400 MHz, DMSO d6) δ ppm 1.31 (s, 9 H), 6.94 (dd, J=7.83, 1.26 Hz, 1 H), 7.16 (dd, J=7.58, 1.26 Hz, 1 H), 7.20-7.27 (m, 2 H), 7.44 (dd, J=8.09, 1.77, 1H), 7.48-7.56 (m, 3 H), 7.79 (dd, J=4.80, 1.51 Hz, 1H), 8.20 (dd, J=7.83, 1.52 Hz, 2 H), 9.04 (dd, J=7.83, 1.52 Hz, 1 H), 10.93 (s, 1 H).

Workup

  1. stirringmixture was stirred for 4 h
  2. customThe reaction mixture was purified by preparative HPLC

Sources & evidence

ORD record
ord-0540154dfeaf44ab840b4e3acc482ae8
Source dataset
uspto-grants-2012_09
Patent number
US08273772B2

Reaction notes

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