Hydrazine → HCID 88439159, compound

HRID 1586500Notes

Reaction equation

HRID 1586500 reaction equation
[CH3:1][C:2]1[C:7]([O:8][CH3:9])=[C:6]([CH3:10])[C:5]([CH2:11][S:12]([C:14]2[N:18]([CH2:19][CH3:20])[C:17]3[CH:21]=[CH:22][C:23]([Cl:25])=[CH:24][C:16]=3[N:15]=2)=[O:13])=[C:4]([N:26]2[C:30](=[O:31])[C:29]3=[CH:32][CH:33]=[CH:34][CH:35]=[C:28]3[C:27]2=[O:36])[CH:3]=1.[NH2:37][NH2:38]>>[Cl:25][C:23]1[CH:22]=[CH:21][C:17]2[N:18]([CH2:19][CH3:20])[C:14]([S:12]([CH2:11][C:5]3[C:6]([CH3:10])=[C:7]([O:8][CH3:9])[C:2]([CH3:1])=[CH:3][C:4]=3[NH:26][C:27]([C:28]3[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=3[C:30]([NH:37][NH2:38])=[O:31])=[O:36])=[O:13])=[N:15][C:16]=2[CH:24]=1

Participants

3

Reactant 2

HCID 9321HydrazineHCID 54314559HCID 54314559, compound

Product 1

HCID 88439159HCID 88439159, compoundYield 57%

Procedure

2-[(4,6-Dimethyl-5-methoxy-2-phthalimidylphenyl)methylsulfinyl]-5-chloro-1-ethyl-1H-benzimidazole (Example 121) (66 mg, 0.13 mmol) was treated with hydrazine according to the procedure of Example 39 to give the crude acyl hydrazide as an oil which was triturated with ether to give the partially deprotected amine as the title compound (28 mg, 57%). 1H NMR δ1.29, (t, 3H), 2.26 (s, 3H), 2.34 (s, 3H), 3.66 (s, 3H), 4.16 (s, 2H), 4.29 (m, 2H), 4.95 (q, 2H), 7.24 (s, 2H), 7.37 (s, 1H), 7.48 (s, 1H), 7.55 (m, 2H), 7.69 (m, 1H), 7.82 (m, 1H), 7.87 (s, 1H).

Workup

  1. customto give the crude acyl hydrazide as an oil which
  2. customwas triturated with ether

Sources & evidence

ORD record
ord-42315995808e491580cef448d1532686
Source dataset
uspto-grants-1999_08
Patent number
US05945425

Reaction notes

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