Water → HCID 68296003, compound

HRID 589971Notes

Reaction equation

HRID 589971 reaction equation
C(OC([N:8]1[C:12]2[N:13]=[CH:14][N:15]=[C:16]([N:17]3[CH2:24][C:21]4([CH2:23][CH2:22]4)[N:20]([S:25](=[O:46])(=[O:45])[N:26]([CH2:36][CH2:37][O:38]C4CCCCO4)[CH2:27][CH2:28][O:29]C4CCCCO4)[CH2:19][CH2:18]3)[C:11]=2[CH:10]=[CH:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O.O.C([O-])(O)=O.[Na+]>C1COCC1>[OH:29][CH2:28][CH2:27][N:26]([CH2:36][CH2:37][OH:38])[S:25]([N:20]1[CH2:19][CH2:18][N:17]([C:16]2[C:11]3[CH:10]=[CH:9][NH:8][C:12]=3[N:13]=[CH:14][N:15]=2)[CH2:24][C:21]21[CH2:23][CH2:22]2)(=[O:46])=[O:45]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 68296050HCID 68296050, compound2×

Product 1

HCID 68296003HCID 68296003, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(4-{Bis-[2-(tetrahydro-pyran-2-yloxy)-ethyl]-sulfamoyl}-4,7-diaza-spiro[2.5]oct-7-yl)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid tert-butyl ester (intermediate 17) was treated with a mixture of TFA (0.5 mL), H2O (0.2 mL) and THF (0.2 mL) at 40° C. for 1 h. The crude reaction mixture was neutralised using sat. NaHCO3 and then extracted with EtOAc (3×10 mL). The combined organic phases were dried (Na2SO4), filtered and concentrated in vacuo. The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

Workup

  1. customThe crude reaction mixture
  2. extractionextracted with EtOAc (3×10 mL)
  3. dry with materialThe combined organic phases were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

Sources & evidence

ORD record
ord-985307467c904db199fe4ce8bd592c75
Source dataset
uspto-grants-2016_01
Patent number
US09233964B2

Reaction notes

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