Hydrochloric Acid → 6-(4-fluoro-2-methoxyphenyl)-1-{[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl}-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride

HRID 1476646Notes

Reaction equation

HRID 1476646 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([CH:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)[C:12](=[O:31])[N:11]([CH2:32][C:33]4[O:37][N:36]=[C:35]([CH2:38][O:39][CH3:40])[N:34]=4)[C:10]=3[CH:9]=2)=[C:4]([O:41][CH3:42])[CH:3]=1.[ClH:43]>O1CCOCC1>[ClH:43].[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([CH:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)[C:12](=[O:31])[N:11]([CH2:32][C:33]4[O:37][N:36]=[C:35]([CH2:38][O:39][CH3:40])[N:34]=4)[C:10]=3[CH:9]=2)=[C:4]([O:41][CH3:42])[CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67258937tert-butyl 4-[6-(4-fluoro-2-methoxyphenyl)-1-{[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl}-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate

Product 1

HCID 672589606-(4-fluoro-2-methoxyphenyl)-1-{[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl}-3-(piperidin-4-yl)thieno[3,2-d]pyrimidine-2,4(1H,3H)-dione hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of tert-butyl 4-[6-(4-fluoro-2-methoxyphenyl)-1-{[3-(methoxymethyl)-1,2,4-oxadiazol-5-yl]methyl}-2,4-dioxo-1,4-dihydrothieno[3,2-d]pyrimidin-3(2H)-yl]piperidine-1-carboxylate (890 mg, compound B62) in 1,4 dioxane (13 ml) is added a solution of hydrogen chloride in 1,4-dioxane (7.4 ml, 4.0 M). The reaction mixture is stirred for 2.5 h at RT. All volatiles are evaporated and the residue is treated with DCM and after removal of the solvent under reduced pressure the title compound is obtained as a solid.

Workup

  1. customAll volatiles are evaporated
  2. additionthe residue is treated with DCM
  3. customafter removal of the solvent under reduced pressure the title compound
  4. customis obtained as a solid

Sources & evidence

ORD record
ord-16c60a439a0c4973a336882f3603660b
Source dataset
uspto-grants-2015_04
Patent number
US09018175B2

Reaction notes

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