7-Methoxy-4,5-dihydronaphtho[1,2-d]thiazol-2-amine → 2-Amino-4,5-dihydronaphtho[1,2-d]thiazol-7-ol

HRID 1506566Notes

Reaction equation

HRID 1506566 reaction equation
C[O:2][C:3]1[CH:4]=[C:5]2[C:14](=[CH:15][CH:16]=1)[C:9]1[N:10]=[C:11]([NH2:13])[S:12][C:8]=1[CH2:7][CH2:6]2>ClCCl>[NH2:13][C:11]1[S:12][C:8]2[CH2:7][CH2:6][C:5]3[C:14](=[CH:15][CH:16]=[C:3]([OH:2])[CH:4]=3)[C:9]=2[N:10]=1

Participants

3

Reactant 1

HCID 6906227-Methoxy-4,5-dihydronaphtho[1,2-d]thiazol-2-amine

Product 1

HCID 866699442-Amino-4,5-dihydronaphtho[1,2-d]thiazol-7-olYield 95.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 7-methoxy-4,5-dihydronaphtho[1,2-d]thiazol-2-amine (15 mg, 0.065 mmol) into dichloromethane (2 mL), cooled to 0° C. was added borontribromide (0.258 mL, 0.258 mmol) slowly at 0° C. The reaction mixture was allowed to warm to room temperature and stirred at room temperature overnight. The reaction mixture was quenched by the slow addition of a few drops of MeOH and purified by prep. HPLC (Luna 5 u C18 21.2*100 mm column; 0%-100% 10mins gradient; Solvent A: 10% MeOH-90% H2O-0.1% TFA; Solvent B: 90% MeOH-90% H2O-0.1% TFA). The desired fractions were collected, concentrated and dried under vacuum to provide 13.5 mg of the title compound as a white solid. LC/MS M+1=219.1. The product had an HPLC retention time=1.51 min. (condition A). 1H NMR (400 MHz, CD3OD) δ ppm 7.35 (1H, d, J=8.36 Hz), 6.71-6.83 (2H, m), 3.04 (2H, d, J=8.14 Hz), 2.78-2.90 (2H, m).

Workup

  1. additionwas added borontribromide (0.258 mL, 0.258 mmol) slowly at 0° C
  2. customThe reaction mixture was quenched by the slow addition of a few drops of MeOH
  3. custompurified by prep
  4. customHPLC (Luna 5 u C18 21.2*100 mm column; 0%-100% 10mins gradient; Solvent A: 10% MeOH-90% H2O-0.1% TFA; Solvent B: 90% MeOH-90% H2O-0.1% TFA)
  5. customThe desired fractions were collected
  6. concentrationconcentrated
  7. customdried under vacuum

Sources & evidence

ORD record
ord-f9701774335c45e68dc8d470bd57ecf6
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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