Dichloromethane → HCID 53497452, compound

HRID 1852974Notes

Reaction equation

HRID 1852974 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH:18]([CH2:23][C:24]([NH2:26])=O)[CH2:19][C:20]([NH2:22])=O)[CH:17]=3)[N:10]3[CH:27]=[CH:28][N:29]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1.C(Cl)Cl.C(N(CC)CC)C.ClC(Cl)(Cl)C(Cl)=O>CN(C=O)C>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][N:16]([CH:18]([CH2:23][C:24]#[N:26])[CH2:19][C:20]#[N:22])[CH:17]=3)[N:10]3[CH:27]=[CH:28][N:29]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6420Trichloroacetyl chlorideHCID 8471Triethylamine2×HCID 674577573-(4-(7-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)pentanediamide

Product 1

HCID 53497452HCID 53497452, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(4-(7-(1-Methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)pentanediamide (0.047 g, 0.12 mmol) was partially dissolved in DMF (0.3 mL) and DCM (0.5 mL) and triethylamine (0.08 g, 0.79 mmol) was added. 2,2,2-trichloroacetyl chloride (0.08 g, 0.44 mmol) was added at 0° C., and the reaction was stirred for 1 hour. Additional reagents (40 mg Et3N and 30 mg acid chloride) were added and the reaction was complete. The reaction was concentrated and pumped to dryness. A minimum amount of water was added (1.5 mL) to dissolve the crude product. Excess sodium chloride was added to the aqueous layer and this mixture was extracted with EtOAc (10×10 mL) to recover the desired product. The organic phase was dried using MgSO4 and concentrated to provide 3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)pentanedinitrile (42 mg, 98% yield). MS (apci) m/z=358.1 (M+H). 1H NMR (d6-DMSO) δ 9.12 (s, 1H), 8.59 (s, 1H), 8.41 (s, 1H), 8.25 (s, 1H), 8.17 (s, 1H), 7.78 (s, 1H), 7.76 (s, 1H), 5.30-5.29 (m, 1H), 3.91 (s, 3H), 1.22-1.10 (m, 4H).

Workup

  1. concentrationThe reaction was concentrated
  2. additionA minimum amount of water was added (1.5 mL)
  3. dissolutionto dissolve the crude product
  4. additionExcess sodium chloride was added to the aqueous layer
  5. extractionthis mixture was extracted with EtOAc (10×10 mL)
  6. customto recover the desired product
  7. customThe organic phase was dried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-41b6f4b3461144958456d61ab5d58290
Source dataset
uspto-grants-2015_02
Patent number
US08962596B2

Reaction notes

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