Carbonate Ion → HCID 86706470, compound

HRID 919602Notes

Reaction equation

HRID 919602 reaction equation
C[Si](C)(C)CCOC[N:7]1[C:11]2=[N:12][CH:13]=[N:14][C:15]([NH:16][CH:17]3[CH2:23][CH2:22][CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18]3)=[C:10]2[CH:9]=[N:8]1.Cl.CCO.C(=O)([O-])[O-]>CO>[NH:19]1[CH2:20][CH2:21][CH2:22][CH2:23][CH:17]([NH:16][C:15]2[N:14]=[CH:13][N:12]=[C:11]3[NH:7][N:8]=[CH:9][C:10]=23)[CH2:18]1

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 21887872Ethanol hydrochlorideHCID 86706469HCID 86706469, compound

Product 1

HCID 86706470HCID 86706470, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

Tert-butyl 3-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino)azepane-1-carboxylate (0.5 g, 1.1 mmol) was dissolved conc HCl:EtOH (1:3, 10 mL) and the solution was heated to 60° C. for 4 h. The reaction mixture was concentrated in vacuo and the residue obtained was dissolved in MeOH and treated with solid supported carbonate resin to neutralize the solution. The reaction mixture stirred for 2 h and filtered off slurry, washed solid with MeOH (2×20 mL). The filtrate was concentrated in vacua to afford the titled intermediate (200 mg, 80%), which was used in the next step without further purification. LCMS: m/z [M+1]=233.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue obtained
  3. additiontreated with solid
  4. filtrationfiltered off slurry
  5. washwashed solid with MeOH (2×20 mL)
  6. concentrationThe filtrate was concentrated in vacua

Sources & evidence

ORD record
ord-3bce2d5950074fd49037f0e286698e1a
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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