Hydrochloric Acid → HCID 178492001, compound

HRID 1244325Notes

Reaction equation

HRID 1244325 reaction equation
COC[N:4]1[C:8]2=[N:9][C:10]([N:13]3[CH2:18][CH2:17]O[CH2:15][CH2:14]3)=[CH:11][CH:12]=[C:7]2[N:6]=[C:5]1[C:19]1[S:20][C:21]2[C:27]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[CH:26][CH:25]=[C:24]([O:34][CH3:35])[C:22]=2[N:23]=1.Cl>>[CH3:35][O:34][C:24]1[C:22]2[N:23]=[C:19]([C:5]3[NH:4][C:8]4=[N:9][C:10]([N:13]5[CH2:18][CH2:17][CH2:15][CH2:14]5)=[CH:11][CH:12]=[C:7]4[N:6]=3)[S:20][C:21]=2[C:27]([N:28]2[CH2:33][CH2:32][O:31][CH2:30][CH2:29]2)=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 11352458HCID 11352458, compound

Product 1

HCID 178492001HCID 178492001, compound

Procedure

0.07 g 3-Methoxymethyl-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-5-morpholin-4-yl-3H-imidazo[4,5-b]pyridine (0.15 mmol) was treated with 5N HCl (2 ml) at 90° C. for 1.5 h. The reaction mixture was concentrated, taken up in water (3 ml) and adjusted to pH 10 with ammonium hydroxide (25%), whereupon a precipitation formed. The precipitation was filtered and the crystals were triturated in hot ethanol. After drying in vacuo 0.025 g 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-5-pyrrolidin-4-yl-3H-imidazo[4,5-b]pyridine (39%) was obtained as a yellow solid; M.p.: 264–268° C.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customadjusted to pH 10 with ammonium hydroxide (25%), whereupon a precipitation
  3. customformed
  4. customThe precipitation
  5. filtrationwas filtered
  6. customthe crystals were triturated in hot ethanol
  7. dry with materialAfter drying in vacuo 0.025 g 2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-5-pyrrolidin-4-yl-3H-imidazo[4,5-b]pyridine (39%)
  8. customwas obtained as a yellow solid

Sources & evidence

ORD record
ord-0f6fc06e4a034ab598d39b45f68aab3b
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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