HCID 86663986, compound → Ethyl 1-[5-[7-acetyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

HRID 712274Notes

Reaction equation

HRID 712274 reaction equation
C([O:3][C:4]([C:6]1[C:14]2[S:13][C:12]([NH:15][C:16](=[O:20])[NH:17][CH2:18][CH3:19])=[N:11][C:10]=2[CH:9]=[C:8]([C:21]2[CH:22]=[N:23][C:24]([N:27]3[CH2:32][CH2:31][C:30]([CH3:38])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:29][CH2:28]3)=[N:25][CH:26]=2)[CH:7]=1)=[CH2:5])C>C1COCC1.O>[C:4]([C:6]1[C:14]2[S:13][C:12]([NH:15][C:16](=[O:20])[NH:17][CH2:18][CH3:19])=[N:11][C:10]=2[CH:9]=[C:8]([C:21]2[CH:26]=[N:25][C:24]([N:27]3[CH2:28][CH2:29][C:30]([CH3:38])([C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH2:31][CH2:32]3)=[N:23][CH:22]=2)[CH:7]=1)(=[O:3])[CH3:5]

Participants

4

Reactant 1

HCID 86663986HCID 86663986, compound

Product 1

HCID 86663987Ethyl 1-[5-[7-acetyl-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylateYield 64%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-[5-[7-(1-ethoxyvinyl)-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate was dissolved in THF (24 mL) and water (6 mL). Sulfonic acid resin MP (200 mg, 3.2 mmol/g) was added and the reaction stirred at rt for 1 h, after which time LCMS indicated clean conversion to the ketone. The reaction mixture was filtered and the solvent removed in vacuo to give a solid which was triturated with Et2O to give the desired product as a yellow solid (600 mg, 64% yield over 2 steps).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed in vacuo
  3. customto give a solid which
  4. customwas triturated with Et2O

Sources & evidence

ORD record
ord-2512eb0de1da46cca680d2157468d639
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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