Hydrogen Bromide → HCID 136367419, compound

HRID 913354Notes

Reaction equation

HRID 913354 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:22][C:21]([CH2:23][CH2:24][CH3:25])=[N:20][C:14]=3[C:15]([NH2:19])=[N:16][C:17]=2[CH:18]=1)C1C=CC=CC=1.Br.[OH-].[Na+]>C(O)(=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13]3[S:22][C:21]([CH2:23][CH2:24][CH3:25])=[N:20][C:14]=3[C:15]([NH2:19])=[N:16][C:17]=2[CH:18]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 116099597-benzyloxy-2-propylthiazolo[4,5-c]quinolin-4-amine

Product 1

HCID 136367419HCID 136367419, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
65 °C

Procedure

To 7-benzyloxy-2-propylthiazolo[4,5-c]quinolin-4-amine (prepared as described in Example 1, 1.59 g, 4.55 mmol) was added a 30 wt. % solution of hydrogen bromide in acetic acid (25 mL). The resulting solution was heated at 65° C. for 1 h, then cooled in an ice bath. Aqueous NaOH (50% w/w solution) was added slowly until the pH=7 and a light yellow solid formed. The solid was isolated by filtration, dried, and purified by HPFC (silica gel eluting sequentially with 0-10% of a solution comprised of 80% CHCl3, 18% MeOH, and 2% conc. NH4OH (CMA) in chloroform, then 10-35% CMA in chloroform). The appropriate fractions were concentrated to a light yellow solid that was crystallized from toluene containing a small amount of methanol. The light yellow solid was isolated by filtration, washed with cold toluene, and dried at 60° C. in a vacuum oven to provide the acetic acid salt of 7-hydroxy-2-propylthiazolo[4,5-c]quinolin-4-amine (0.64 g, 54%), mp 236-239° C. 1H NMR (300 MHz, d6-DMSO) δ 9.72 (s, 1H), 7.58 (d, J=8.8 Hz, 1H), 6.91 (d, J=2.2 Hz, 1H), 6.78 (dd, J=8.7, 2.2 Hz, 1H), 6.70 (s, 2H), 3.12 (t, J=7.8 Hz, 2H), 1.83 (sextet, J=7.2 Hz, 2H), 0.99 (t, J=7.5 Hz, 3H); 13C NMR (75 MHz, d6-DMSO) δ 168.4, 158.1, 152.2, 146.6, 139.6, 135.6, 125.7, 113.3, 112.2, 108.9, 35.0, 22.8, 13.4; Anal. calcd for C13H13N3OS.0.22C2H4O2: C, 59.23; H, 5.13; N, 15.42. Found: C, 59.42; H, 5.00; N, 15.41.

Workup

  1. temperaturecooled in an ice bath
  2. customa light yellow solid formed
  3. customThe solid was isolated by filtration
  4. customdried
  5. custompurified by HPFC (silica gel eluting sequentially with 0-10% of a solution
  6. concentrationThe appropriate fractions were concentrated to a light yellow solid
  7. customthat was crystallized from toluene containing a small amount of methanol
  8. customThe light yellow solid was isolated by filtration
  9. washwashed with cold toluene
  10. customdried at 60° C. in a vacuum oven

Sources & evidence

ORD record
ord-7eeafecbec22422a9fa6a02399fe4d8b
Source dataset
uspto-grants-2011_09
Patent number
US08026366B2

Reaction notes

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