Methanol → HCID 86664046, compound

HRID 712338Notes

Reaction equation

HRID 712338 reaction equation
[CH2:1]([C:3]1([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:8][CH2:7][N:6]([C:9]2[N:14]=[CH:13][C:12]([C:15]3[CH:16]=[C:17]([CH:34]=[O:35])[C:18]4[S:22][C:21]([N:23]5CN(C)C[N:25]([CH2:30][CH3:31])[C:24]5=[O:32])=[N:20][C:19]=4[CH:33]=3)=[CH:11][N:10]=2)[CH2:5][CH2:4]1)[CH3:2].OS(O)(=O)=O.[C:46]([O-:49])(O)=O.[Na+].[CH3:51]O>C(Cl)Cl>[CH3:51][O:35][CH:34]([O:49][CH3:46])[C:17]1[C:18]2[S:22][C:21]([NH:23][C:24](=[O:32])[NH:25][CH2:30][CH3:31])=[N:20][C:19]=2[CH:33]=[C:15]([C:12]2[CH:11]=[N:10][C:9]([N:6]3[CH2:7][CH2:8][C:3]([CH2:1][CH3:2])([C:36]([O:38][CH2:39][CH3:40])=[O:37])[CH2:4][CH2:5]3)=[N:14][CH:13]=2)[CH:16]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 86664045HCID 86664045, compound

Product 1

HCID 86664046HCID 86664046, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

Ethyl 4-ethyl-1-[5-[2-(3-ethyl-5-methyl-2-oxo-1,3,5-triazinan-1-yl)-7-formyl-1,3-benzothiazol-5-yl]pyrimidin-2-yl]piperidine-4-carboxylate (33 mg, 0.058 mmol) was suspended in MeOH (2 mL) and treated with conc. H2SO4 (˜5 μL). The reaction was heated to 50° C. for 1.5 h then diluted with DCM and sat.NaHCO3(aq). The organic layer was separated and the aqueous layer extracted further with DCM (2×) before the combined DCM extracts were dried and the solvent evaporated to yield the crude product (35 mg). Crude product was used in the next step without further purification. MS: 557.16 [M+H]+.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted further with DCM (2×) before the combined DCM extracts
  3. customwere dried
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-e46f2fc98d7244febf26b99840aa8ff0
Source dataset
uspto-grants-2015_11
Patent number
US09181234B2

Reaction notes

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