Triethylamine → (7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-thiocarbamic acid S-methyl ester

HRID 1678248Notes

Reaction equation

HRID 1678248 reaction equation
[S:1]1[C:5]([C:6]2[CH:7]=[C:8]([NH2:15])[CH:9]=[C:10]3[C:14]=2[NH:13][N:12]=[CH:11]3)=[CH:4][C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2.Cl[C:21]([O:23]C)=[S:22].[CH2:25](N(CC)CC)C>C(O)C>[CH3:25][S:23][C:21](=[O:22])[NH:15][C:8]1[CH:9]=[C:10]2[C:14](=[C:6]([C:5]3[S:1][C:2]4[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=4[CH:4]=3)[CH:7]=1)[NH:13][N:12]=[CH:11]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 554404Methyl chloromethanethioateHCID 59023728HCID 59023728, compound

Product 1

HCID 59023854(7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-thiocarbamic acid S-methyl esterYield 66%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 7-benzo[b]thiophen-2-yl-1H-indazol-5-ylamine (Example #F.8.1, 530 mg, 2.0 mmol) and methyl chlorothioformate (0.25 mL, 2.8 mmol) in ethanol (10 mL) was added triethylamine (0.56 mL, 4.0 mmol). The reaction mixture was stirred at ambient temperature for about 16 hours and the resulting solid was collected by filtration, washed with water (3×50 mL), and dried to yield (7-benzo[b]thiophen-2-yl-1H-indazol-5-yl)-thiocarbamic acid S-methyl ester (448 mg, 66%); LC/MS (Table 1, Method e) Rt 2.14 min; m/z: [M−H]− 338.

Workup

  1. filtrationthe resulting solid was collected by filtration
  2. washwashed with water (3×50 mL)
  3. customdried

Sources & evidence

ORD record
ord-e270663c97304f4bb9384348b20cbc6c
Source dataset
uspto-grants-2011_08
Patent number
US08008481B2

Reaction notes

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