Water → Ethyl cis(+/-)-2-(3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylate

HRID 43542

Reaction equation

HRID 43542 reaction equation
[N:1]([C@H:4]1[C@@H:9]([NH:10][C:11]([C:13]2[NH:14][C:15]([CH2:19][CH3:20])=[C:16]([Cl:18])[N:17]=2)=[O:12])[CH2:8][CH2:7][N:6]([C:21]2[S:22][C:23]3[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)[CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][C@H:4]1[C@@H:9]([NH:10][C:11]([C:13]2[NH:14][C:15]([CH2:19][CH3:20])=[C:16]([Cl:18])[N:17]=2)=[O:12])[CH2:8][CH2:7][N:6]([C:21]2[S:22][C:23]3[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=[CH:28][CH:27]=[CH:26][C:24]=3[N:25]=2)[CH2:5]1

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 86648559Ethyl cis(+/-)-2-(3-azido-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylate

Product 1

HCID 86648558Ethyl cis(+/-)-2-(3-amino-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl cis(±)-2-(3-azido-4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}piperidin-1-yl)-1,3-benzothiazole-7-carboxylate obtained in Example (81d) (84 mg, 0.17 mmol) was dissolved in THF (3 mL). Triphenylphosphine (63 mg, 0.24 mmol) and distilled water (0.2 mL) were added, and the mixture was heated under reflux for 15 hours. The reaction solution was concentrated under reduced pressure and the precipitated solid was collected by filtration, to obtain 59.6 mg of the title compound as a white solid (75%).

Workup

  1. additionwere added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 15 hours
  4. concentrationThe reaction solution was concentrated under reduced pressure
  5. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-527690045b7a411eb4446e5529d147f0
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Linked notes

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