Benzoyl isothiocyanate → tert-butyl 5-chloro-3-[(6-oxo-2-thioxo-1,2,6,7-tetrahydro-3H-purin-3-yl)methyl]-1H-indole-1-carboxylate

HRID 912673Notes

Reaction equation

HRID 912673 reaction equation
[NH2:1][C:2]([C:4]1[NH:8][CH:7]=[N:6][C:5]=1[NH:9][CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([Cl:20])[CH:18]=2)[N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:12]=1)=[O:3].C(N=[C:37]=[S:38])(=O)C1C=CC=CC=1>C(Cl)Cl>[Cl:20][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH:12]=[C:11]2[CH2:10][N:9]1[C:5]2[N:6]=[CH:7][NH:8][C:4]=2[C:2](=[O:3])[NH:1][C:37]1=[S:38]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 67416011HCID 67416011, compound

Product 1

HCID 86631122tert-butyl 5-chloro-3-[(6-oxo-2-thioxo-1,2,6,7-tetrahydro-3H-purin-3-yl)methyl]-1H-indole-1-carboxylateYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of tert-butyl 3-({[5-(aminocarbonyl)-1H-imidazol-4-yl]amino}methyl)-5-chloro-1H-indole-1-carboxylate (0.30 g, 0.78 mmol, obtained from Example 10(b)) and benzoyl isothiocyanate (0.13 mL, 0.94 mmol) in CH2Cl2 (5 mL) was stirred for 2 h and then evaporated. Ammonia (7 M in MeOH, 3 mL) was added to the residue and the mixture was heated to 80° C. for 2 h and then evaporated. Purification by flash chromatography using MeOH (2%) in CHCl3 gave the title compound (0.15 g, 50%). 1H1NMR (DMSO-d6) δ ppm 13.92 (1H), 12.57 (1H), 8.23 (1H), 8.12 (1H), 7.99 (1H), 7.81 (1H), 7.37 (1H), 5.81 (2H), 1.61 (9H); MS (ESI) m/z 430 (M−1).

Workup

  1. customevaporated
  2. additionAmmonia (7 M in MeOH, 3 mL) was added to the residue
  3. customevaporated
  4. customPurification by flash chromatography

Sources & evidence

ORD record
ord-b0ec3cfe42fe4fc7b4b74c591c193187
Source dataset
uspto-grants-2011_09
Patent number
US08026244B2

Reaction notes

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