Hydroxylamine → HCID 178511342, compound

HRID 1170498Notes

Reaction equation

HRID 1170498 reaction equation
[NH2:1][OH:2].[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH2:28][C:29]#[N:30])[C:18]3[S:22][N:21]=[C:20]([N:23]4[CH:27]=[CH:26][N:25]=[CH:24]4)[N:19]=3)=[CH:11][C:6]=2[O:5][CH2:4]1>O.CO>[O:3]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][NH:13][CH2:14][CH2:15][CH2:16][N:17]([C:18]3[S:22][N:21]=[C:20]([N:23]4[CH:27]=[CH:26][N:25]=[CH:24]4)[N:19]=3)[CH2:28][C:29]([NH:1][OH:2])=[NH:30])=[CH:11][C:6]=2[O:5][CH2:4]1

Participants

5

Reactant 2

HCID 787HydroxylamineHCID 11625423HCID 11625423, compound

Product 1

HCID 178511342HCID 178511342, compoundYield 22%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Hydroxylamine (1.0 mL of a 50 wt % in H2O, 15 mmol) was added all at once a solution of [{3-[(benzo[1,3]dioxol-5-ylmethyl)-amino]-propyl}-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-amino]-acetonitrile (30 mg, 75 μmol) in MeOH (1.0 mL) at r.t. The reaction mixture stirred at r.t. for 30 h prior to concentrating to a white solid. The residue was purified using column chromatography (CH2Cl2 to 4:1 CH2Cl2/MeOH) to afford 7.0 mg (22%) of 2-[{3-[(benzo[1,3]dioxol-5-ylmethyl)-amino]-propyl}-(3-imidazol-1-yl-[1,2,4]thiadiazol-5-yl)-amino]-N-hydroxy-acetamidine as a white solid. [M+H]+ 430.91; 1H NMR (400 MHz, CD3OD) δ 8.39 (s, 1H), 7.79 (s, 1H), 7.76 (s, 1H), 7.07 (s, 1H), 6.82 (s, 1H), 6.76-6.70 (m, 2H), 5.89 (s, 2H), 4.19 (s, 2H), 3.65 (s, 2H), 3.58 (m, 2H), 2.63 (t, 2H), 1.94 (tt, 2H).

Workup

  1. concentrationto concentrating to a white solid
  2. customThe residue was purified

Sources & evidence

ORD record
ord-187eed313b38416fa7ff0f73ee2ebf84
Source dataset
uspto-grants-2010_11
Patent number
US07825256B2

Reaction notes

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