Ethanol → HCID 178452080, compound

HRID 624721Notes

Reaction equation

HRID 624721 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][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18][CH2:17]3)[N:12]3[N:29]=[CH:30][C:31]([CH:32]=O)=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1.C(O)C.[NH:37]1[CH2:43][C:41](=[O:42])[NH:40][C:38]1=[O:39].N1CCCCC1>O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[CH:14]=[C:13]([NH:15][CH:16]3[CH2:17][CH2:18][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23])[CH2:20][CH2:21]3)[N:12]3[N:29]=[CH:30][C:31]([CH:32]=[C:43]4[C:41](=[O:42])[NH:40][C:38](=[O:39])[NH:37]4)=[C:11]3[N:10]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8082PiperidineHCID 10006HydantoinHCID 58314734HCID 58314734, compound

Product 1

HCID 178452080HCID 178452080, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To the reaction flask, tert-butyl 4-(5-(3-chlorophenylamino)-3-formylpyrazolo[1,5-a]pyrimidin-7-ylamino)piperidine-1-carboxylate (811 mg, 1.7 mmol) was added to ethanol (6.3 mL) along with hydantoin (172 mg, 1.7 mmol) and piperidine (170 μL, 1.7 mmol). The reaction was heated at 80° C. for 12 hours then cooled to room temperature and diluted with water. The solid was collected by filtration, washed with water and cold ethanol. The material was dried under vacuum overnight. The product, tert-butyl 4-(5-(3-chlorophenylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-7-ylamino)piperidine-1-carboxylate, was recovered as a red solid in 67% yield after further purification by recrystallization from ethyl acetate/hexanes. LCMS (M+1=553)

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationThe solid was collected by filtration
  3. washwashed with water and cold ethanol
  4. customThe material was dried under vacuum overnight
  5. customThe product, tert-butyl 4-(5-(3-chlorophenylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-7-ylamino)piperidine-1-carboxylate, was recovered as a red solid in 67% yield
  6. customafter further purification
  7. customby recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-6453eae34eef4924908229e6b3b6a6fd
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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