HCID 44466646, compound → HCID 76770971, compound

HRID 241627Notes

Reaction equation

HRID 241627 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:19]3[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=3)[C:9]3[C:14]([C:15]=2[S:16][C:17]#[N:18])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:26])[O:4][N:3]=1.[NH2:27][OH:28].C([O-])(O)=O.[Na+]>CS(C)=O.O.CCOC(C)=O.C(OCC)C>[OH:28][N:27]=[C:17]([S:16][C:15]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([C:19]2[CH:20]=[CH:21][C:22]([OH:25])=[CH:23][CH:24]=2)[C:7]=1[C:6]1[C:2]([CH3:1])=[N:3][O:4][C:5]=1[CH3:26])[NH2:18]

Participants

7

Reactant 2

HCID 44466646HCID 44466646, compoundHCID 86656236hydroxylamine NaHCO3

Product 1

HCID 76770971HCID 76770971, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

4-(2-(3,5-Dimethylisoxazol-4-yl)-3-thiocyanato-1H-indol-1-yl)phenol was dissolved in DMSO and 10 eq 2 M hydroxylamine/NaHCO3 (aq) stock solution was added. The reaction was stirred at 65° C. overnight and then diluted with H2O. A precipitation was formed after stirring for 5 min. The mixture was diluted with EtOAc and diethylether, washed with NH4Cl (aq) and phases were partitioned. Organic phase was evaporated to dryness in vacuo and subjected to purification on reverse phase preparative HPLC to provide the title compound 2-(3,5-dimethylisoxazol-4-yl)-1-(4-hydroxyphenyl)-1H-indol-3-yl N′-hydroxycarbamimidothioate (E32). ES/MS m/z: 395.17 (M+H), 393.19 (M−H); 1H NMR (acetone-d6, 500 MHz): 8.88 (broad s, 1H), 8.73 (broad s, 1H), 7.80-7.78 (m, 1H), 7.29-7.24 (m, 3H), 7.18 (d, 2H), 6.95 (d, 2H), 5.11 (broad s, 2H), 2.28 (s, 3H), 2.00 (s, 3H)

Workup

  1. customA precipitation
  2. customwas formed
  3. stirringafter stirring for 5 min
  4. washwashed with NH4Cl (aq) and phases
  5. customwere partitioned
  6. customOrganic phase was evaporated to dryness in vacuo
  7. customsubjected to purification on reverse phase preparative HPLC

Sources & evidence

ORD record
ord-98bc84a2ec694cb8965ead80ba4fe3c6
Source dataset
uspto-grants-2014_02
Patent number
US08653072B2

Reaction notes

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