Acetic Acid → HCID 89445309, compound

HRID 2173668Notes

Reaction equation

HRID 2173668 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]2[S:8][C:9]3[C:13]([NH2:14])=[N:12][NH:11][C:10]=3[C:5]2=[C:4]([CH3:15])[CH:3]=1.[CH3:16][C:17]([CH3:19])=O.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl.C(Cl)Cl>[CH:17]([NH:14][C:13]1[C:9]2[S:8][C:6]3[C:5]([C:10]=2[NH:11][N:12]=1)=[C:4]([CH3:15])[CH:3]=[C:2]([CH3:1])[N:7]=3)([CH3:19])[CH3:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 71516705HCID 71516705, compound

Product 1

HCID 89445309HCID 89445309, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

The 6,8-dimethyl-1H-pyrazolo[3′,4′:4,5]thieno[2,3-b]pyridin-3-amine (75 mg, 0.34 mmol) was stirred in DCE (3.4 mL). To this solution was added acetone (0.08 mL, 1.03 mmol) and acetic acid (0.060 mL, 1.03 mmol). The mixture was stirred 15 minutes, then NaBH(AcO)3 (150 mg, 0.70 mmol) was added. The resulting slurry was stirred about 2 hrs. LC/MS indicates the reaction is complete. The reaction was diluted with DCM (15 mL) and quenched with aqueous 2N NaOH. The aqueous layer was separated and extracted with DCM. The combined organic layers were dried over Na2SO4, and concentrated under vacuum to give a crude residue. The residue was purified by trituration with MeOH to give the pure product, 30 mg, (33%), as a light tan solid. 1H NMR (400 MHz, DMSO-d6): δ ppm 7.09 (s, 1H), 5.65 (bs, 1H), 3.61 (bs, 1H), 2.63 (s, 3H), 2.50 (s, 3H), 1.17 (d, J=6.32, 6H). LC/MS: RT=0.55 min., m/z=261.0 [M+H]+.

Workup

  1. stirringThe resulting slurry was stirred about 2 hrs
  2. customquenched with aqueous 2N NaOH
  3. customThe aqueous layer was separated
  4. extractionextracted with DCM
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b4a640c4b0494b47a81c3ce334729c26
Source dataset
uspto-grants-2015_06
Patent number
US09056876B2

Reaction notes

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