Ethylenediamine → HCID 178489380, compound

HRID 886581Notes

Reaction equation

HRID 886581 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:24]([C:26]4[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=4)[OH:25])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[N:11](COCC[Si](C)(C)C)[N:10]=1.FC(F)(F)C(O)=O.C(N)CN>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:17]2[C:12](=[N:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:24]([C:26]4[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][N:27]=4)[OH:25])[CH:21]=[CH:22][CH:23]=3)[CH:16]=2)[NH:11][N:10]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 59825045{3-[3-(2-methoxy-phenyl)-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-(3-methyl-pyridin-2-yl)-methanol

Product 1

HCID 178489380HCID 178489380, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The material from step 1 was dissolved in dichloromethane and 1 mL of trifluoroacetic acid was added. The resulting mixture was left at room temperature for 6 h. The solvent was then completely evaporated and the residue dissolved in dichloromethane. 0.5 mL (450 mg, 7.5 mmol) of ethylene diamine was added. After 2 h at room temperature the mixture was evaporated and the crude purified by mass-triggered reverse-phase HPLC to afford 52 mg (0.12 mmol, 14%) of {3-[3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-phenyl}-(3-methyl-pyridin-2-yl)-methanol as an off-white solid. 1H-NMR (500 MHz, DMSO-d6) a 8.80 (d, 1H), 8.42 (d(d), 1H), 8.27 (d, 1H), 7.71 ((t), br. 1H), 7.68 (dd, 1H), 7.62 (d(m), 1H), 7.57 (d(m), 1H), 7.47 (dd(d), 1H), 7.43 (t, 1H), 7.34 (d(m), 1H), 7.26-7.23 (m, 2H), 7.10 (ddd, 1H), 5.99 (s, 1H), 3.84 (s, 3H), 2.27 (s, 3H) (exchangeable protons not visible in 1H-NMR); MS: m/z 423.2 (M+H+).

Workup

  1. customThe solvent was then completely evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. customAfter 2 h at room temperature the mixture was evaporated
  4. customthe crude purified by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-13a87052ec104a41b604a77a9b686e0b
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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