Sodium Methoxide → 7-benzyloxy-2-propylthiazolo[4,5-c]quinolin-4-amine

HRID 913350Notes

Reaction equation

HRID 913350 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:28][C:27]([CH2:29][CH2:30][CH3:31])=[N:26][C:14]=3[C:15]([NH:19]C(=O)C(Cl)(Cl)Cl)=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:28][C:27]([CH2:29][CH2:30][CH3:31])=[N:26][C:14]=3[C:15]([NH2:19])=[N:16][C:17]=2[CH:18]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67392739HCID 67392739, compound

Product 1

HCID 116099597-benzyloxy-2-propylthiazolo[4,5-c]quinolin-4-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a magnetically stirred mixture of N-(7-benzyloxy-2-propylthiazolo[4,5-c]quinolin-4-yl)-2,2,2-trichloroacetamide (prepared as described above in Part H, 6.96 g, 14.9 mmol) in methanol (100 mL) at rt was added NaOMe (25 wt. % solution in MeOH, 11.3 mL, 52.1 mmol). After a few minutes a solution formed from which a solid precipitated. The reaction mixture was concentrated in vacuo and dried under vacuum. The resulting solid was suspended in a minimal amount of methanol (50 mL) and was isolated by filtration. The solid was washed with methanol to provide 7-benzyloxy-2-propylthiazolo[4,5-c]quinolin-4-amine as a light yellow solid in high purity (3.93 g, 76%), mp 175-178° C. 1H NMR (300 MHz, d6-DMSO) δ 7.67 (d, J=8.7 Hz, 1H), 7.49-7.29 (m, 5H), 7.10 (d, J=2.5 Hz, 1H), 6.96 (dd, J=8.7, 2.5 Hz, 1H), 6.84 (s, 2H), 5.20 (s, 2H), 3.09 (t, J=7.8 Hz, 2H), 1.84 (sextet, J=7.2 Hz, 2H), 0.99 (t, J=7.5 Hz, 3H); 13C NMR (75 MHz, d6-DMSO) δ 169.1, 158.9, 152.4, 146.5, 139.4, 137.0, 136.0, 128.4, 127.8, 127.6, 125.7, 113.3, 113.2, 107.8, 69.3, 35.1, 22.8, 13.5. MS (APCI) m/z=350.0 (M+H) % Anal. calcd for C20H19N3OS: C, 68.74; H, 5.48; N, 12.02. Found: C, 68.62; H, 5.74; N, 11.94.

Workup

  1. customAfter a few minutes a solution formed from which a solid
  2. customprecipitated
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. customdried under vacuum
  5. customwas isolated by filtration
  6. washThe solid was washed with methanol

Sources & evidence

ORD record
ord-4b5fe399384d4fd8b5cb129db2dbd524
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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