Diisopropylethylamine → HCID 60151084, compound

HRID 1406020Notes

Reaction equation

HRID 1406020 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[NH:11][C:12]([C:14]1[C:18]2[CH2:19][CH2:20][CH2:21][C:22]3[C:23](=[N:24][C:25]([NH:28][C:29]4[CH:37]=[CH:36][C:32]([C:33]([OH:35])=O)=[CH:31][C:30]=4[O:38][CH3:39])=[N:26][CH:27]=3)[C:17]=2[N:16]([CH3:40])[N:15]=1)=[O:13])[CH3:2].CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[CH3:72][N:73]1[CH2:78][CH2:77][CH:76]([NH2:79])[CH2:75][CH2:74]1>CN(C=O)C.O>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[NH:11][C:12]([C:14]1[C:18]2[CH2:19][CH2:20][CH2:21][C:22]3[C:23](=[N:24][C:25]([NH:28][C:29]4[CH:37]=[CH:36][C:32]([C:33](=[O:35])[NH:79][CH:76]5[CH2:77][CH2:78][N:73]([CH3:72])[CH2:74][CH2:75]5)=[CH:31][C:30]=4[O:38][CH3:39])=[N:26][CH:27]=3)[C:17]=2[N:16]([CH3:40])[N:15]=1)=[O:13])[CH3:10]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27375314-Amino-1-methylpiperidineHCID 60150944HCID 60150944, compound

Product 1

HCID 60151084HCID 60151084, compoundYield 73.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 4-({3-[(2,6-diethylphenyl)carbamoyl]-1-methyl-1,4,5,6-tetrahydropyrazolo[4′,3′:6,7]cyclohepta[1,2-d]pyrimidin-9-yl}amino)-3-methoxybenzoic acid (50 mg, 0.092 mmol) in anhydrous DMF (0.5 mL) was treated with DIPEA (0.150 mL) and TBTU (50 mg, 0.150 mmol). The mixture was then treated with 1-methylpiperidin-4-amine (18 mg, 1.38 mmol) and was stirred at room temperature for 2 hours. The reaction was diluted with water and extracted twice with DCM. The organic layer was dried over Na2SO4 and the solvent was evaporated to dryness. The crude solid was purified by flash chromatography on silica gel (DCM/MeOH) to afford 43 mg (72% yield) of the title compound.

Workup

  1. extractionextracted twice with DCM
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customthe solvent was evaporated to dryness
  4. customThe crude solid was purified by flash chromatography on silica gel (DCM/MeOH)

Sources & evidence

ORD record
ord-7145aee6a5e940e58965094bec422615
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

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