Hydrochloric Acid → 4-(4-Chloro-5-(2,6-dimethyl-8-(pentan-3-yl)imidazo[1,2-b]pyridazin-3-yl)thiazol-2-yl)morpholine hydrochloride

HRID 1432638Notes

Reaction equation

HRID 1432638 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[S:5][C:6]=1[C:7]1[N:11]2[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:19][CH3:20])[CH2:17][CH3:18])[C:10]2=[N:9][C:8]=1[CH3:22].Cl>CC(O)C>[ClH:1].[Cl:1][C:2]1[N:3]=[C:4]([N:23]2[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)[S:5][C:6]=1[C:7]1[N:11]2[N:12]=[C:13]([CH3:21])[CH:14]=[C:15]([CH:16]([CH2:17][CH3:18])[CH2:19][CH3:20])[C:10]2=[N:9][C:8]=1[CH3:22]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 115462553-(4-Chloro-2-morpholinothiazol-5-yl)-2,6-dimethyl-8-(pentan-3-yl)imidazo[1,2-b]pyridazine

Product 1

HCID 1296265764-(4-Chloro-5-(2,6-dimethyl-8-(pentan-3-yl)imidazo[1,2-b]pyridazin-3-yl)thiazol-2-yl)morpholine hydrochlorideYield 187,596.297%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
50 °C

Procedure

IPA (225.0 mL) is added to compound N-{4-chloro-5-[8-(1-ethyl-propyl)-2,6-dimethyl-imidazo[1,2-b]pyridazin-3-yl]-thiazol-2-yl}-morpholine (18.8 g, 0.0448 mmol, below) in a 1 L 1-neck round-bottomed flask The starting material slurry is heated to 50° C. on a Buchi bath, at which time a hazy solution resulted. Concentrated (12 M) aqueous HCl (3.73 mL, 0.0448 mmole, 1.0 eq) is added all at once, and the hazy solution is stirred at 50° C. on the Buchi for 10 minutes, then evaporated to a yellow solid under vacuum. After 20 minutes at room temperature under vacuum (weight of 20.9 g), acetone (100 mL) is added and the resulting yellow slurry is stirred at room temperature for 1 hour, then cooled with an ice bath and stirred for an additional 1 hour. The slurry is filtered, rinsed with acetone, and dried overnight under vacuum at 40° C. to provide pale yellow-white crystalline solid 19.18 g (94%). 1H NMR (DMSO): δ 7.52 (s, 1H), 3.73 (t, J=4.6, 4H), 3.49 (t, J=5.2 Hz, 4H), 3.39 (m, 1H), 2.57 (s, 3H), 2.49 (s, 3H), 1.77 (m, 4H), 0.80 (t, J=7.4 Hz, 6H).

Workup

  1. customresulted
  2. additionis added all at once, and the hazy solution
  3. customevaporated to a yellow solid under vacuum
  4. additionAfter 20 minutes at room temperature under vacuum (weight of 20.9 g), acetone (100 mL) is added
  5. stirringthe resulting yellow slurry is stirred at room temperature for 1 hour
  6. temperaturecooled with an ice bath
  7. stirringstirred for an additional 1 hour
  8. filtrationThe slurry is filtered
  9. washrinsed with acetone
  10. customdried overnight under vacuum at 40° C.

Sources & evidence

ORD record
ord-d0864b3b167745eb9434d822cc8509ae
Source dataset
uspto-grants-2009_11
Patent number
US07612067B2

Reaction notes

Loading…