Ethylenediamine → HCID 57868874, compound

HRID 1692955Notes

Reaction equation

HRID 1692955 reaction equation
[CH3:1][C:2]1([CH3:31])[CH2:5][C:4]([CH2:28][C:29]#[N:30])([N:6]2[CH:10]=[C:9]([C:11]3[C:12]4[CH:19]=[CH:18][N:17](COCC[Si](C)(C)C)[C:13]=4[N:14]=[CH:15][N:16]=3)[CH:8]=[N:7]2)[CH2:3]1.FC(F)(F)C(O)=O.C(N)CN>CO>[CH3:1][C:2]1([CH3:31])[CH2:5][C:4]([CH2:28][C:29]#[N:30])([N:6]2[CH:10]=[C:9]([C:11]3[C:12]4[CH:19]=[CH:18][NH:17][C:13]=4[N:14]=[CH:15][N:16]=3)[CH:8]=[N:7]2)[CH2:3]1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 6422Trifluoroacetic acidHCID 67279657HCID 67279657, compound

Product 1

HCID 57868874HCID 57868874, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3,3-Dimethyl-1-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclobutylacetonitrile (0.020 g, 0.000046 mol) was treated with trifluoroacetic acid (0.5 mL, 0.006 mol) at rt for 30 min and then evaporated to dry. The residue was then shaked with ethylenediamine (0.2 mL, 0.003 mol) in MeOH (1 mL) for 2 h. The reaction was concentrated and purified on prep HPLC (XBridge C18 column, eluting with a gradient of acetonitrile/water containing 0.15% NH4OH) to give the desired prodcut. LCMS calculated for C17H19N6(M+H)+: 307.2; Found: 307.3. 1H NMR (400 MHz, DMSO-d6): δ 12.10 (1H, br s), 8.76 (1H, s), 8.67 (1H, s), 8.40 (1H, s), 7.58 (1H, d, J=3.6 Hz), 7.05 (1H, d, J=3.6 Hz), 3.35 (2H, s), 2.75 (2H, d, J=14 Hz), 2.33 (2H, d, J=14.0 Hz), 1.22 (3H, s), 1.02 (3H, s) ppm.

Workup

  1. customevaporated
  2. customto dry
  3. concentrationThe reaction was concentrated
  4. custompurified on prep HPLC (XBridge C18 column
  5. washeluting with a gradient of acetonitrile/water containing 0.15% NH4OH)
  6. customto give the desired prodcut

Sources & evidence

ORD record
ord-9200edc118284553984e7efecae99300
Source dataset
uspto-grants-2012_04
Patent number
US08158616B2

Reaction notes

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