Hydrochloric Acid → HCID 178492002, compound

HRID 1244328Notes

Reaction equation

HRID 1244328 reaction equation
COC[N:4]1[C:8]2=[N:9][C:10]([N:13]3[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]3)=[CH:11][CH:12]=[C:7]2[N:6]=[C:5]1[C:20]1[S:21][C:22]2[C:28]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:27][CH:26]=[C:25]([O:35][CH3:36])[C:23]=2[N:24]=1.Cl>>[CH3:36][O:35][C:25]1[C:23]2[N:24]=[C:20]([C:5]3[NH:4][C:8]4=[N:9][C:10]([N:13]5[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]5)=[CH:11][CH:12]=[C:7]4[N:6]=3)[S:21][C:22]=2[C:28]([N:29]2[CH2:34][CH2:33][O:32][CH2:31][CH2:30]2)=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 21919247HCID 21919247, compound

Product 1

HCID 178492002HCID 178492002, compound

Procedure

0.035 g 1-[3-Methoxymethyl-2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl]-piperidin-4-ol (0.07 mmol) was treated with 5N HCl (1 ml) at 90° C. for 0.5 h. The reaction mixture was concentrated, taken up in water (1 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 0.018 g 1-[2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl]-piperidin-4-ol (56%) was obtained as a yellow solid; M.p.: 228–230° 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 0.018 g 1-[2-(4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-3H-imidazo[4,5-b]pyridin-5-yl]-piperidin-4-ol (56%)
  8. customwas obtained as a yellow solid

Sources & evidence

ORD record
ord-f10e092fe2614e929271303028f6ff0d
Source dataset
uspto-grants-2006_10
Patent number
US07122545B2

Reaction notes

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