Sodium Iodide → HCID 57642253, compound

HRID 2113316Notes

Reaction equation

HRID 2113316 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:37])[CH2:11][N:12]2[N:18]=[C:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[N:14]([CH2:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[C:13]2=[O:36])[CH:6]=[CH:7][CH:8]=1.[NH2:38][C:39]([NH2:41])=[S:40].[Na+].[I-]>CC(C)=O>[C:39]([S:40][CH2:2][C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:37])[CH2:11][N:12]2[N:18]=[C:17]([CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)[C:16]3[CH:25]=[CH:26][CH:27]=[CH:28][C:15]=3[N:14]([CH2:29][C:30](=[O:35])[C:31]([CH3:34])([CH3:33])[CH3:32])[C:13]2=[O:36])[CH:6]=[CH:7][CH:8]=1)(=[NH:38])[NH2:41]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 2723790ThioureaHCID 68839571HCID 68839571, compound

Product 1

HCID 57642253HCID 57642253, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

N-(3-Chloromethyl-phenyl)-2-[5-cyclohexyl-1-(3,3-dimethyl-2-oxo-butyl)-2-oxo-1,2-dihydro-3H-1,3,4-benzotriazepin-3-yl]-acetamide (Example 49, step a) (52 mg, 0.0 mmol) was reacted with thiourea (7.6 mg, 0.0 mmol) and NaI (2 mg) in refluxing acetone (10 ml) for 3 h. After cooling, the solvents were concentrated in vacuo, affording the title compound as a yellow solid after trituration with Et2O (18 mg, 30%). 1H NMR (DMSO-d6) 9.89 (1H, br s), 8.99 (3H, br s), 7.75-7.46 (3H, m), 7.29-7.04 (5H, m), 4.77 (2H, m), 4.40 (2H, m), 4.38 (1H, m), 3.93 (1H, m), 2.86 (1H, m), 1.73-1.64 (6H, m), 1.21-1.08 (13H, m).

Workup

  1. temperatureAfter cooling
  2. concentrationthe solvents were concentrated in vacuo

Sources & evidence

ORD record
ord-75f60dca666148d1a2d1ec48bf33cc48
Source dataset
uspto-grants-2009_04
Patent number
US07524837B2

Reaction notes

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