Acetic Acid → HCID 178448508, compound

HRID 624728Notes

Reaction equation

HRID 624728 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]3)[N:12]3[N:22]=[CH:23][C:24]([CH:25]=[C:26]4[NH:30][C:29](=[O:31])[NH:28][C:27]4=[O:32])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:33]C(O)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH2:51]1[CH2:55]OC[CH2:52]1>>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:21][CH2:20][N:19]([CH2:33][CH:51]([CH3:52])[CH3:55])[CH2:18][CH2:17]3)[N:12]3[N:22]=[CH:23][C:24]([CH:25]=[C:26]4[NH:30][C:29](=[O:31])[NH:28][C:27]4=[O:32])=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydrideHCID 178518511HCID 178518511, compound

Product 1

HCID 178448508HCID 178448508, compound

Procedure

To 5-((5-(3-chlorophenylamino)-7-(piperidin-4-ylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione (30 mg, 0.06 mmol) in THF and AcOH (4.8 mg, 0.08 mmol) was added isobutryldehyde (2.2 mL, 0.2 mmol) and sodium triacetoxy borohydride (85.0 mg, 0.4 mmol). The mixture was stirred at room temperature for 0.5 hour. The mixture was concentrated, diluted with MeOH, and purified by prep HPLC to yield 5-((5-(3-chlorophenylamino)-7-(1-isobutylpiperidin-4-ylamino)pyrazolo[1,5-a]pyrimidin-3-yl)methylene)imidazolidine-2,4-dione. LCMS (M+1=509)

Workup

  1. concentrationThe mixture was concentrated
  2. additiondiluted with MeOH
  3. custompurified by prep HPLC

Sources & evidence

ORD record
ord-c69b4d766e684c6aaaf2107c962cef2b
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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