(R)-1-(3-chlorophenyl)ethanamine → 5-[1-(3-chlorophenyl)ethylamino]-7-(cyclopropylamino)-3-[(2,5-dioxoimidazolidin-4-ylidene)methyl]pyrazolo[1,5-a]pyrimidine-6-carbonitrile

HRID 624819Notes

Reaction equation

HRID 624819 reaction equation
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=[C:15]4[C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16]4)=[C:9]3[N:8]=[C:7](S(C)(=O)=O)[C:6]=2[C:26]#[N:27])[CH2:3][CH2:2]1.C1(NC2N3N=CC(C=C4C(=O)NC(=O)N4)=C3N=C(S(C)=O)C=2C#N)CC1.[Cl:54][C:55]1[CH:56]=[C:57]([C@H:61]([NH2:63])[CH3:62])[CH:58]=[CH:59][CH:60]=1>C(O)(C)C>[Cl:54][C:55]1[CH:56]=[C:57]([CH:61]([NH:63][C:7]2[C:6]([C:26]#[N:27])=[C:5]([NH:4][CH:1]3[CH2:3][CH2:2]3)[N:10]3[N:11]=[CH:12][C:13]([CH:14]=[C:15]4[C:19](=[O:20])[NH:18][C:17](=[O:21])[NH:16]4)=[C:9]3[N:8]=2)[CH3:62])[CH:58]=[CH:59][CH:60]=1

Participants

5

Reactant 3

HCID 2507697(R)-1-(3-chlorophenyl)ethanamineHCID 1785046137-(cyclopropylamino)-3-[(2,5-dioxoimidazolidin-4-ylidene)methyl]-5-methylsulfinylpyrazolo[1,5-a]pyrimidine-6-carbonitrileHCID 1785048347-(cyclopropylamino)-3-[(2,5-dioxoimidazolidin-4-ylidene)methyl]-5-methylsulfonylpyrazolo[1,5-a]pyrimidine-6-carbonitrile

Product 1

HCID 1784633795-[1-(3-chlorophenyl)ethylamino]-7-(cyclopropylamino)-3-[(2,5-dioxoimidazolidin-4-ylidene)methyl]pyrazolo[1,5-a]pyrimidine-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

The mixture of 7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)-5-(methylsulfonyl)pyrazolo[1,5-a]pyrimidine-6-carbonitrile and 7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)-5-(methylsulfinyl)pyrazolo[1,5-a]pyrimidine-6-carbonitrile (20 mg) was mixed with (R)-1-(3-chlorophenyl)ethanamine (33 mg) in i-propanol (0.5 mL). The reaction mixture was heated at 90° C. in the microwave for 1 hour. The reaction was cooled to room temperature and concentrated under vacuum. The residue was diluted with water, filtered and washed with water followed by 20% ethanol/water mixture. The solid was dried under high vacuum to give 2 mg of the product, 5-(1-(3-chlorophenyl)ethylamino)-7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidine-6-carbonitrile. LCMS (M+1=463)

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. additionThe residue was diluted with water
  4. filtrationfiltered
  5. washwashed with water
  6. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-b6bfc6453ce540c992f51ddcea97624a
Source dataset
uspto-grants-2016_04
Patent number
US09303033B2

Reaction notes

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