Phenethylamine → HCID 59129008, compound

HRID 2390503Notes

Reaction equation

HRID 2390503 reaction equation
[CH2:1](CN)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:10]([N:13](C(C)C)CC)(C)C.Cl.Cl[CH2:21][C:22]([NH2:24])=[NH:23].[C:25]([C:29]1[CH:44]=[CH:43][CH:42]=[CH:41][C:30]=1[O:31][C:32]1[C:37]([N:38]=[C:39]=[S:40])=[CH:36][CH:35]=[CH:34][N:33]=1)([CH3:28])([CH3:27])[CH3:26].CCOC(/N=N/C(OCC)=O)=O>CN(C=O)C>[CH2:1]([N:13]([CH2:21][C:22]1[N:24]=[C:39]([NH:38][C:37]2[C:32]([O:31][C:30]3[CH:41]=[CH:42][CH:43]=[CH:44][C:29]=3[C:25]([CH3:28])([CH3:26])[CH3:27])=[N:33][CH:34]=[CH:35][CH:36]=2)[S:40][N:23]=1)[CH3:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 1001PhenethylamineHCID 81531DiisopropylethylamineHCID 27769572-Chloroacetamidine monohydrochlorideHCID 5462977Diethyl azodicarboxylateHCID 59857388HCID 59857388, compound

Product 1

HCID 59129008HCID 59129008, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of N-benzylmethylamine (68 μL, 0.53 mmol), diisopropylethylamine (187 μL, 1.06 mmol) and chloroacetamidine hydrochloride (68 mg, 0.53 mmol) in DMF (5 mL) was stirred at rt for 18 h. 2-(2-tert-butylphenoxy)-3-isothiocyanatopyridine (Example 1a) (150 mg, 0.53 mmol) was then added and mixture was stirred for 3 h at 80° C. The reaction mixture was cooled to rt and diethylazodicarboxylate (168 μL, 1.06 mmol) was added and mixture was stirred for 2 h. The reaction mixture was purified by preparative HPLC to give Example 94 (2 mg, 2TFA salt) as a white. (M+H)+=460. 1H NMR (400 MHz, DMSO d6) δ ppm 1.30 (s, 9 H), 2.26 (s, 3H), 3.64 (s, 2H), 3.67 (s, 2H), 6.92 (dd, J=7.83, 1.26 Hz, 1H), 7.12-7.39 (m, 9 H), 7.42 (dd, J=7.83, 1.52, 1H), 7.76 (dd, J=5.05, 1.26, 1H), 8.89 (d, J=7.58 Hz, 1H), 10.82 (s, 1 H).

Workup

  1. stirringmixture was stirred for 3 h at 80° C
  2. temperatureThe reaction mixture was cooled to rt
  3. stirringmixture was stirred for 2 h
  4. customThe reaction mixture was purified by preparative HPLC
  5. customto give Example 94 (2 mg, 2TFA salt) as a white

Sources & evidence

ORD record
ord-0355e3fc0fa54fd190e5338a7f843ecb
Source dataset
uspto-grants-2012_09
Patent number
US08273772B2

Reaction notes

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