1-Hydroxybenzotriazole → HCID 54157151, compound

HRID 1816323Notes

Reaction equation

HRID 1816323 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][O:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[S:25][C:24]4=[N:26][C:27]([C:29]5[CH:37]=[CH:36][C:32]([C:33]([OH:35])=[O:34])=[CH:31][CH:30]=5)=[CH:28][N:23]4[N:22]=3)=[CH:17][CH:16]=2)[CH2:11][CH2:10]1.O[N:39]1[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[N:41]=[N:40]1.Cl.C(N=C=NCCCN(C)C)C>ClCCl>[N:39]1([O:34][C:33](=[O:35])[C:32]2[CH:31]=[CH:30][C:29]([C:27]3[N:26]=[C:24]4[N:23]([CH:28]=3)[N:22]=[C:21]([C:18]3[CH:17]=[CH:16][C:15]([N:12]5[CH2:11][CH2:10][CH:9]([O:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][O:2][CH3:1])[CH2:14][CH2:13]5)=[CH:20][CH:19]=3)[S:25]4)=[CH:37][CH:36]=2)[C:43]2[CH:44]=[CH:45][CH:46]=[CH:47][C:42]=2[N:41]=[N:40]1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 224929354-[2-[4-[4-(5-Methoxypentyloxy)-piperidin-1-yl]phenyl]imidazo[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid

Product 1

HCID 54157151HCID 54157151, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 (1.28 g) and 1-hydroxybenzotriazole (465 mg) in dichloromethane (50 ml) was added 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (WSCD.HCl) (943 mg), and the mixture was stirred overnight at ambient temperature. The reaction mixture was evaporated in vacuo. To the resulting precipitate was added water (50 ml) and filtered. The precipitate was washed with water and IPE (50 ml) and dried under reduced pressure for 3 hours to give 4-[2-[4-[4-(5-methoxypentyloxy)piperidin-1-yl]phenyl]imidazo-[2,1-b][1,3,4]thiadiazol-6-yl]benzoic acid benzotriazol-1-yl ester (1.26 g).

Workup

  1. customThe reaction mixture was evaporated in vacuo
  2. additionTo the resulting precipitate was added water (50 ml)
  3. filtrationfiltered
  4. washThe precipitate was washed with water and IPE (50 ml)
  5. customdried under reduced pressure for 3 hours

Sources & evidence

ORD record
ord-31e6efdd33604b019226cf8f8da95408
Source dataset
uspto-grants-2005_04
Patent number
US06884774B2

Reaction notes

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