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

HRID 712264Notes

Reaction equation

HRID 712264 reaction equation
C([O:3][C:4]([C:6]1([CH3:34])[CH2:11][CH2:10][N:9]([C:12]2[N:17]=[CH:16][C:15]([C:18]3[CH:19]=[C:20]([Br:33])[C:21]4[S:25][C:24]([NH:26][C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[N:23][C:22]=4[CH:32]=3)=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])C.[OH-].[Na+].CCO.Cl>C1COCC1>[Br:33][C:20]1[C:21]2[S:25][C:24]([NH:26][C:27]([NH:29][CH2:30][CH3:31])=[O:28])=[N:23][C:22]=2[CH:32]=[C:18]([C:15]2[CH:16]=[N:17][C:12]([N:9]3[CH2:8][CH2:7][C:6]([CH3:34])([C:4]([OH:5])=[O:3])[CH2:11][CH2:10]3)=[N:13][CH:14]=2)[CH:19]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14798Sodium HydroxideHCID 86663956Ethyl 1-(5-(7-bromo-2-(3-ethylureido)benzo[d]thiazol-5-yl)pyrimidin-2-yl)-4-methylpiperidine-4-carboxylate

Product 1

HCID 866639571-[5-[7-Bromo-2-(ethylcarbamoylamino)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylic acidYield 33.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

1-{5-[7-Bromo-2-(3-ethyl-ureido)-benzothiazol-5-yl]-pyrimidin-2-yl}-4-methyl-piperidine-4-carboxylic acid ethyl ester (50 mg) was dissolved in THF (1 mL) and 1 M aq NaOH (1 mL) added. The mixture was heated to 70° C. overnight. LCMS showed approx 50% conversion to product. EtOH (0.5 mL) was added and heating continued for a further 6 h. The mixture was acidified to pH 3 with 1 M HCl (aq) and concentrated under reduced pressure. The mixture was suspended in ˜10% MeOH in DCM and filtered through a syringe filter. The filtrate was concentrated in vacuo to give the desired product as an off-white solid (16 mg) which was used in the next step with no further purification. m/z: 519/521 [M+H]+.

Workup

  1. temperatureheating
  2. concentrationconcentrated under reduced pressure
  3. filtrationfiltered through a syringe
  4. filtrationfilter
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-268b71e486dc4e3f9f0ca414695ea5d8
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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