1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68512052, compound

HRID 2241399Notes

Reaction equation

HRID 2241399 reaction equation
[CH3:1][O:2][C:3]1[CH:35]=[CH:34][C:6]([CH2:7][N:8]2[C:12]3=[N:13]C=[CH:15][C:16](OC4C=CC(N)=CC=4F)=[C:11]3[C:10]([NH:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH:29]([OH:33])[CH2:28]3)=[N:9]2)=[CH:5][CH:4]=1.FC1C=CC(N2C(=[O:49])C(C(O)=O)=CC=N2)=CC=1.CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.O>CN(C=O)C.O.CCN(CC)CC>[CH3:1][O:2][C:3]1[CH:35]=[CH:34][C:6]([CH2:7][N:8]2[CH:15]=[CH:16][C:11]([C:12]([NH2:13])=[O:49])=[C:10]([NH:26][CH:27]3[CH2:32][CH2:31][CH2:30][CH:29]([OH:33])[CH2:28]3)[NH:9]2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667671712-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acidHCID 685142403-(1-(4-methoxybenzyl)-4-(4-amino-2-fluorophenoxy)-1H-pyrazolo[3,4-b]pyridin-3-ylamino)cyclohexanol

Product 1

HCID 68512052HCID 68512052, compoundYield 97.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

A solution of 3-(1-(4-methoxybenzyl)-4-(4-amino-2-fluorophenoxy)-1H-pyrazolo[3,4-b]pyridin-3-ylamino)cyclohexanol (50 mg, 0.10 mmol), 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (74 mg, 0.31 mmol, obtained from Example 19 Step C), EDCI (120 mg, 0.63 mmol), Et3N (0.1 mL) and HOBT-H2O (96 mg, 0.63 mmol) was stirred in DMF (1 mL) for 10 hours. The reaction mixture was poured into water and extracted with CH2Cl2. The organic layer washed with saturated aqueous NaHCO3, 10% aqueous LiCl, dried with Na2SO4, filtered and concentrated. The residue was purified with flash silica gel chromatography (5% MeOH in CH2Cl2) to afford the product (35 mg, 48% yield) as a brown solid. LRMS (APCI pos) m/e 694.2 (M+H).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer washed with saturated aqueous NaHCO3, 10% aqueous LiCl
  3. dry with materialdried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with flash silica gel chromatography (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-08064c14767a4b848a06cb534c36bfa2
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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