Hydrochloric Acid → HCID 59540752, compound

HRID 1677531Notes

Reaction equation

HRID 1677531 reaction equation
COC[O:4][C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]3[C:24]([C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:23][N:22]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:19]3=[N:20][CH:21]=2)[CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:10]=1.Cl.C(OCC)(=O)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[OH:4][C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]3[C:24]([C:25](=[O:30])[C:26]([CH3:29])([CH3:27])[CH3:28])=[CH:23][N:22]([CH2:31][O:32][CH2:33][CH2:34][Si:35]([CH3:38])([CH3:37])[CH3:36])[C:19]3=[N:20][CH:21]=2)[CH:8]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 59540613HCID 59540613, compound

Product 1

HCID 59540752HCID 59540752, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-[2-(3-methoxymethoxy-5-pyrrolidin-1-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one (492 mg, 0.91 mmol) in CH2Cl2 (1.5 ml) was added a solution of 10% ethanolic hydrogen chloride (4 ml, dry). The flask was capped and stirred for 2.5 hours. The volatile material was stripped (rotovap). Ethyl acetate (25 ml) and aqueous 5% Na2CO3 (25 ml) was added and the 2 phase system vigorously stirred for 3 minutes. The material was partitioned and the organic phase collected and washed with brine (25 ml). The aqueous phases were back extracted with EtOAc (2×20 ml). The organics were combined, dried (MgSO4), filtered and stripped to provide a crude semi-solid. The material was purified by preparative TLC, eluting with 38% ethyl acetate in hexanes to afford 326 mg of 1-[2-(3-hydroxy-5-pyrrolidin-1-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow-brown solid.

Workup

  1. customThe flask was capped
  2. stirringthe 2 phase system vigorously stirred for 3 minutes
  3. customThe material was partitioned
  4. customthe organic phase collected
  5. washwashed with brine (25 ml)
  6. extractionThe aqueous phases were back extracted with EtOAc (2×20 ml)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customto provide a crude semi-solid
  10. customThe material was purified by preparative TLC
  11. washeluting with 38% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-cda433e1ff804a85a6aad63e99da4af6
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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