Water → 1-(5-(2-(3-Ethylureido)-7-(pyridin-2-yl)benzothiazol-5-yl)pyridazin-3-yl)-4-methylpiperidine-4-carboxylic acid

HRID 712327Notes

Reaction equation

HRID 712327 reaction equation
[CH2:1]([NH:3][C:4](=[O:39])[NH:5][C:6]1[S:7][C:8]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:13][C:12]([C:21]3[CH:22]=[C:23]([N:27]4[CH2:32][CH2:31][C:30]([CH3:38])([C:33]([O:35]CC)=[O:34])[CH2:29][CH2:28]4)[N:24]=[N:25][CH:26]=3)=[CH:11][C:9]=2[N:10]=1)[CH3:2].CC(C)([O-])C.[K+].O>CS(C)=O>[CH2:1]([NH:3][C:4](=[O:39])[NH:5][C:6]1[S:7][C:8]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=3)=[CH:13][C:12]([C:21]3[CH:22]=[C:23]([N:27]4[CH2:32][CH2:31][C:30]([CH3:38])([C:33]([OH:35])=[O:34])[CH2:29][CH2:28]4)[N:24]=[N:25][CH:26]=3)=[CH:11][C:9]=2[N:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86664038Ethyl 1-(5-(2-(3-ethylureido)-7-(pyridin-2-yl)benzo[d]thiazol-5-yl)pyridazin-3-yl)-4-methylpiperidine-4-carboxylate

Product 1

HCID 866640391-(5-(2-(3-Ethylureido)-7-(pyridin-2-yl)benzothiazol-5-yl)pyridazin-3-yl)-4-methylpiperidine-4-carboxylic acidYield 53%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To an ice-cold solution of ethyl 1-(5-(2-(3-ethylureido)-7-(pyridin-2-yl)benzo[d]thiazol-5-yl)pyridazin-3-yl)-4-methylpiperidine-4-carboxylate (0.05 g, 0.092 mmol) in DMSO (2 mL) was added potassium tert-butoxide (0.051 g, 0.45 mmol) and the mixture stirred at rt for 2 h. After completion of reaction (by TLC), water (10 mL) was added followed by extraction with EtOAc (3×50 mL) and the organic layer discarded. The pH of the aqueous layer was adjusted up to 4-5, extracted with EtOAc (3×50 mL) and the combined organic layer dried over Na2SO4, filtered and evaporated under reduced pressure. The residue thus obtained was triturated with ether to obtain Compound 195 as an off-white solid (0.025 g, 53%). 1H NMR (DMSO-d6): δ 9.15 (s, 1H), 8.82 (m, 1H), 8.55 (d, J=8.0 Hz, 1H), 8.38 (s, 1H), 8.21 (s, 1H), 8.02 (t, J=8.0 Hz, 1H), 7.90 (m, 1H), 7.64 (s, 1H), 7.46 (m, 1H), 7.17 (br s, 1H), 4.20 (m, 2H), 3.19-3.24 (m, 4H), 2.10 (m, 2H), 1.43 (m, 2H), 1.22 (s, 3H) and 1.01 (t, J=7.2 Hz, 3H). MS: 518.29 [M+H]+.

Workup

  1. additionwas added
  2. extractionfollowed by extraction with EtOAc (3×50 mL)
  3. extractionextracted with EtOAc (3×50 mL)
  4. dry with materialthe combined organic layer dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue thus obtained
  8. customwas triturated with ether

Sources & evidence

ORD record
ord-d05d9b99cba84919b05ce1a4db0a1334
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

Loading…