Triethylamine → 3-(9-((2-((2,3-dimethyl-2H-indazol-6-yl)amino)-5-methylpyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)-3-oxopropanenitrile

HRID 1056651Notes

Reaction equation

HRID 1056651 reaction equation
[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[C:6]([NH:12][C:13]3[N:18]=[C:17]([NH:19][CH:20]4[CH2:30][CH2:29][C:23]5([CH2:28][CH2:27][NH:26][CH2:25][CH2:24]5)[CH2:22][CH2:21]4)[C:16]([CH3:31])=[CH:15][N:14]=3)[CH:7]=[CH:8]2)=[N:3]1.C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.[C:60]([CH2:62][C:63](O)=[O:64])#[N:61]>C(Cl)Cl.CN(C=O)C>[CH3:1][N:2]1[C:10]([CH3:11])=[C:9]2[C:4]([CH:5]=[C:6]([NH:12][C:13]3[N:18]=[C:17]([NH:19][CH:20]4[CH2:30][CH2:29][C:23]5([CH2:28][CH2:27][N:26]([C:63](=[O:64])[CH2:62][C:60]#[N:61])[CH2:25][CH2:24]5)[CH2:22][CH2:21]4)[C:16]([CH3:31])=[CH:15][N:14]=3)[CH:7]=[CH:8]2)=[N:3]1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 9740Cyanoacetic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 118406574N2-(2,3-dimethyl-2H-indazol-6-yl)-5-methyl-N4-(3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamine

Product 1

HCID 1183901743-(9-((2-((2,3-dimethyl-2H-indazol-6-yl)amino)-5-methylpyrimidin-4-yl)amino)-3-azaspiro[5.5]undecan-3-yl)-3-oxopropanenitrileYield 20.5%

Reagents, catalysts & solvents 1

HCID 22350042dichloromethane N,N-dimethylformamideSolvent

Procedure

To a solution of N2-(2,3-dimethyl-2H-indazol-6-yl)-5-methyl-N4-(3-azaspiro[5.5]undecan-9-yl)pyrimidine-2,4-diamine (203.2 mg, 0.4843 mmol), HOAT (105.8 mg, 0.7773 mmol) and EDCI (144.5 mg, 0.7538 mmol) in DCM/DMF (4 mL/1 mL) were added N,N-diethylethanamine (209.1 mg, 2.066 mmol) and 2-cyanoacetic acid (48.1 mg, 0.565 mmol). The reaction was stirred at rt for 2.5 h and then concentrated in vacuo. The residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1) to give the title compound as a light pink solid (48.4 mg, 20.4%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by silica gel column chromatography (DCM/MeOH (v/v)=30/1)

Sources & evidence

ORD record
ord-f9dadb5409e84c61a41af159c647a119
Source dataset
uspto-grants-2016_07
Patent number
US09399637B2

Reaction notes

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