Water → 1-[5-[2-(Ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acid

HRID 712312Notes

Reaction equation

HRID 712312 reaction equation
[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]#[CH:17])=[CH:14][C:13]([C:18]3[CH:19]=[N:20][C:21]([N:24]4[CH2:29][CH2:28][C:27]([CH3:35])([C:30]([O:32]CC)=[O:31])[CH2:26][CH2:25]4)=[N:22][CH:23]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2].CC(C)([O-])C.[K+].O>CS(C)=O>[CH2:1]([NH:3][C:4]([NH:6][C:7]1[S:8][C:9]2[C:15]([C:16]#[CH:17])=[CH:14][C:13]([C:18]3[CH:23]=[N:22][C:21]([N:24]4[CH2:25][CH2:26][C:27]([CH3:35])([C:30]([OH:32])=[O:31])[CH2:28][CH2:29]4)=[N:20][CH:19]=3)=[CH:12][C:10]=2[N:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 23665647Potassium tert-butoxideHCID 86663977Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Product 1

HCID 569535781-[5-[2-(Ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acidYield 87%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To an ice-cold solution of ethyl 1-[5-[2-(ethylcarbamoylamino)-7-ethynyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (1.1 g, 2.23 mmol) in DMSO (10 mL) was added potassium tert-butoxide (1.25 g, 11.1 mmol) and the mixture stirred at rt for 1 h. After completion of reaction (by TLC), water (100 mL) was added, followed by extraction with EtOAc (2×100 mL) and the organic layer then discarded. The pH of the aqueous layer was adjusted up to 4-5, extracted with hot EtOAc (3×100 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 the desired product as off-white solid (0.9 g, 87% yield). 1H NMR (DMSO-d6): δ 1.14 (t, J=7.20 Hz, 3H), 1.21 (s, 3H), 1.42 (m, 2H), 2.04 (m, 2H), 3.20 (m, 2H), 3.33 (q, J=7.20, 2H), 4.25 (m, 2H), 4.67 (s, 1H), 6.80 (br s, 1H), 7.61 (s, 1H), 7.94 (s, 1H); 8.86 (s, 2H), 10.78 (br s, 1H) and 12.46 (br, s, 1H).

Workup

  1. additionwas added
  2. extractionfollowed by extraction with EtOAc (2×100 mL)
  3. extractionextracted with hot EtOAc (3×100 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-da395364a73341b3994dc247948f362a
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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