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

HRID 712325Notes

Reaction equation

HRID 712325 reaction equation
[CH2:1]([N:3]1CN(C)C[N:5]([C:10]2[S:11][C:12]3[C:18]([CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:17][C:16]([C:25]4[CH:26]=[N:27][C:28]([N:31]5[CH2:36][CH2:35][C:34]([CH3:42])([C:37]([O:39]CC)=[O:38])[CH2:33][CH2:32]5)=[N:29][CH:30]=4)=[CH:15][C:13]=3[N:14]=2)[C:4]1=[O:43])[CH3:2].[OH-].[Na+].Cl>CCO>[CH2:1]([NH:3][C:4]([NH:5][C:10]1[S:11][C:12]2[C:18]([CH2:19][O:20][CH2:21][CH2:22][O:23][CH3:24])=[CH:17][C:16]([C:25]3[CH:26]=[N:27][C:28]([N:31]4[CH2:32][CH2:33][C:34]([CH3:42])([C:37]([OH:39])=[O:38])[CH2:35][CH2:36]4)=[N:29][CH:30]=3)=[CH:15][C:13]=2[N:14]=1)=[O:43])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66977375Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(2-methoxyethoxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Product 1

HCID 866640371-[5-[2-(Ethylcarbamoylamino)-7-(2-methoxyethoxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acidYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

Ethyl 1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-(2-methoxyethoxymethyl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (86 mg, 0.141 mmol) was dissolved in EtOH (15 mL) and 2M aqueous NaOH (5 mL) added. The reaction was then stirred at 70° C. for 2 h then cooled to rt, 2M HCl (10 mL) was added and the mixture was stirred for 1 h. The mixture was then extracted with EtOAc (3×25 mL) and the combined organic fractions, washed with brine, separated, dried (Na2SO4) and concentrated under reduced pressure to afford Compound 202 (60 mg, 81%) as an off-white solid. 1H NMR (DMSO-d6): δ=12.40 (bs, 1H), 10.76 (bs, 1H), 8.75 (s, 2H), 7.82 (d, J=1.5 Hz, 1H), 7.41 (d, J=1.4 Hz, 1H), 6.84 (bt, J=5.4 Hz, 1H), 4.68 (s, 2H), 4.28 (dt, J=13.8 and 4.2 Hz, 2H), 3.39-3.30 (m, 2H), 3.35 (s, 3H), 3.25-3.17 (m, 2H), 2.05-2.00 (m, 2H), 1.39 (ddd, J=13.8, 10.2 and 3.9 Hz, 2H), 1.20 (s, 3H), 1.12 (t, J=7.2 Hz, 3H). MS: 529.16 [M+H]+.

Workup

  1. temperaturethen cooled to rt
  2. stirringthe mixture was stirred for 1 h
  3. extractionThe mixture was then extracted with EtOAc (3×25 mL)
  4. washthe combined organic fractions, washed with brine
  5. customseparated
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-38ac352a3f5e41eaa372e2ad36687edc
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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