Hydrochloric Acid → 4-[2-[4-[4-(5-Methoxypentyloxy)-piperidin-1-yl]phenyl]imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid

HRID 1816698Notes

Reaction equation

HRID 1816698 reaction equation
FC(F)(F)C(O)=O.C([O:10][C:11](=[O:46])[C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:19]=[C:20]3[N:24]([CH:25]=2)[N:23]=[C:22]([C:26]2[CH:31]=[CH:30][C:29]([N:32]4[CH2:37][CH2:36][CH:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][O:44][CH3:45])[CH2:34][CH2:33]4)=[CH:28][CH:27]=2)[S:21]3)=[CH:14][CH:13]=1)C.O.Cl>CO.O1CCCC1>[CH3:45][O:44][CH2:43][CH2:42][CH2:41][CH2:40][CH2:39][O:38][CH:35]1[CH2:34][CH2:33][N:32]([C:29]2[CH:28]=[CH:27][C:26]([C:22]3[S:21][C:20]4=[N:19][C:18]([C:15]5[CH:14]=[CH:13][C:12]([C:11]([OH:46])=[O:10])=[CH:17][CH:16]=5)=[CH:25][N:24]4[N:23]=3)=[CH:31][CH:30]=2)[CH2:37][CH2:36]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 69677627HCID 69677627, compound

Product 1

HCID 224929354-[2-[4-[4-(5-Methoxypentyloxy)-piperidin-1-yl]phenyl]imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acidYield 81.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-[2-[4-[4-(5-methoxypentyloxy)piperidin-1-yl]phenyl]imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid ethyl ester trifluroacetic acid salt (2.01 g) in a mixture of methanol (40 ml) and tetrahydrofuran (20 ml) was added 4N-NaOR (20 ml), and the mixture was refluxed for 6 hours. The reaction mixture was cooled, poured into water (200 ml) and adjusted to pH 2 with conc. HCl. The resulting precipitate was collected by filtration, washed in turn with water, isopropyl alcohol (30 ml) and IPE (50 ml) to give 4-[2-[4-[4-(5-methoxypentyloxy)piperidin-1-yl]phenyl]imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid (1.28 g).

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed in turn with water, isopropyl alcohol (30 ml) and IPE (50 ml)

Sources & evidence

ORD record
ord-b3f709bd2b964cb3b462fb3abde9f316
Source dataset
uspto-grants-2005_04
Patent number
US06884868B1

Reaction notes

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