Hydrochloric Acid → HCID 66780320, compound

HRID 1958052Notes

Reaction equation

HRID 1958052 reaction equation
[Cl:1][C:2]1[C:3]([CH3:34])=[C:4]([CH2:8][N:9]([C:21]2[N:22]=[C:23]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[S:24][C:25]=2[C:26]#[N:27])[C:10](=O)[CH2:11][NH:12]C(=O)OC(C)(C)C)[CH:5]=[CH:6][CH:7]=1.B1([O-])O[O:36]1.O.O.O.O.[Na+].Cl.O1CCOCC1>CO.O.CCOC(C)=O>[NH2:12][CH2:11][C:10]1[N:9]([CH2:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[C:3]=2[CH3:34])[C:21]2[N:22]=[C:23]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[S:24][C:25]=2[C:26](=[O:36])[N:27]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrateHCID 68048061HCID 68048061, compound

Product 1

HCID 66780320HCID 66780320, compoundYield 26%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
55 °C

Procedure

To a solution of 1,1-dimethylethyl (2-{[(3-chloro-2-methylphenyl)methyl][5-cyano-2-(4-morpholinyl)-1,3-thiazol-4-yl]amino}-2-oxoethyl)carbamate (150 mg, 0.296 mmol) in Methanol (5 mL) and Water (5.00 mL) was added sodium perborate tetrahydrate (137 mg, 0.889 mmol). The mixture was stirred at 55° C. for 2 hr and then diluted in 100 mL EtOAc. After washed with 100 mL H2O, the organic layer was concentrated and diluted in 10 mL DCM, to which was added 4M HCl in dioxane (0.371 mL, 1.482 mmol). The mixture was stirred at rt for 17 hr. One fourth of the crude material was purified by HPLC and then treated with HCl (6N) to give the titled compound 9 mg (26%). LC/MS (ES) m/z=406.4 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 7.42-7.40 (d, 1H, J=8.0 Hz), 7.18-7.12 (m, 1H), 6.55 (d, 1H, J=8.0 Hz), 5.65 (s, 2H), 4.21 (s, 2H), 3.79-3.76 (m, 4H), 3.68-3.62 (m, 4H), 2.52 (s, 3H).

Workup

  1. washAfter washed with 100 mL H2O
  2. concentrationthe organic layer was concentrated
  3. additiondiluted in 10 mL DCM, to which
  4. stirringThe mixture was stirred at rt for 17 hr
  5. customOne fourth of the crude material was purified by HPLC
  6. additiontreated with HCl (6N)

Sources & evidence

ORD record
ord-cbb9861324a14e1abfeb8a92dcdc871c
Source dataset
uspto-grants-2013_04
Patent number
US08410095B2

Reaction notes

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