Phenethylamine → 3-(1-Aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-1-benzyl-1-methyl-thiourea

HRID 14692

Reaction equation

HRID 14692 reaction equation
C([N:3]([CH2:6]C)[CH2:4][CH3:5])C.[C:8](Cl)(Cl)=[S:9].[NH2:12][C:13]1[C:22]2[C:17](=[C:18]([O:25][CH3:26])[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=2)[C:16]([CH2:27][N:28]2C(=O)C3C(=CC=CC=3)C2=O)=[N:15][CH:14]=1.[CH2:39]([CH2:46]N)[C:40]1C=CC=[CH:42][CH:41]=1>ClCCl>[NH2:28][CH2:27][C:16]1[C:17]2[C:22](=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[O:25][CH3:26])[C:13]([NH:12][C:8](=[S:9])[N:3]([CH2:4][C:5]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:46]=2)[CH3:6])=[CH:14][N:15]=1

Participants

6

Reactant 4

HCID 1001PhenethylamineHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 593410902-(4-Amino-6,8-dimethoxy-isoquinolin-1-ylmethyl)-isoindole-1,3-dione

Product 1

HCID 593410723-(1-Aminomethyl-6,8-dimethoxy-isoquinolin-4-yl)-1-benzyl-1-methyl-thioureaYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (46 μL, 0.33 mmol) and then thiophosgene (13 μL, 0.16 mmol) were added to a solution of Example 45C (40 mg, 0.11 mol) in dichloromethane (3 mL), and the reaction stirred for 1 h at r.t. N-benzylmethylamine (46 μL, 0.33 mmol) was added, and the reaction stirred for 1 h. Solvent was removed in vacuo, and the residue was deprotected with a solution of hydrazine (0.1 mL) in ethanol (4 mL), stirring for 1 h. Purification by Prep-HPLC gave 18 mg (39%) of the title compound (TFA salt) as a yellow solid. H1-NMR (MeOD-d4): δ 8.15 (s, 1H), 7.22-7.38 (m, 5H), 6.70 (s, 1H), 6.66 (s, 1H), 5.18 (s, 2H), 4.58 (s, 2H), 3.96 (s, 3H), 3.81 (s, 3H), 3.23 (s, 3H). MS (ES) (M+H) calc'd for C21H24N4O2S, 397; found 397.

Workup

  1. stirringthe reaction stirred for 1 h
  2. customSolvent was removed in vacuo
  3. stirringstirring for 1 h
  4. customPurification by Prep-HPLC

Sources & evidence

ORD record
ord-37fe3da4ac1f45b6b20bca988a913546
Source dataset
uspto-grants-2010_06
Patent number
US07732446B1

Linked notes

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