Acetic Acid → HCID 178448508, compound

HRID 2036950Notes

Reaction equation

HRID 2036950 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-dc7488ad47714bffbc88f074484dfe1e
Source dataset
uspto-grants-2013_11
Patent number
US08575177B2

Reaction notes

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