1,2-Dichloroethane → HCID 70865475, compound

HRID 1628334Notes

Reaction equation

HRID 1628334 reaction equation
[CH2:1]([N:3]1[C:7]([NH2:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[N:4]1)[CH3:2].[C:15]([NH:22][C@H:23]([C:31](O)=[O:32])[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(Cl)CCl>CN(C)C1C=CN=CC=1.ClCCl>[CH2:1]([N:3]1[C:7]([NH:8][C:31](=[O:32])[C@@H:23]([NH:22][C:15](=[O:16])[O:17][C:18]([CH3:19])([CH3:20])[CH3:21])[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)=[N:4]1)[CH3:2]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 67497493HCID 67497493, compound

Product 1

HCID 70865475HCID 70865475, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a 25 ml flask was added 1-ethyl-3-(pyridin-4-yl)-1H-pyrazol-5-amine 20.2.0 (283 mg, 1.50 mmole), Boc-L-phenylalanine (439 mg, 1.65 mmole), EDC (375 mg, 1.95 mmole), 4-dimethylaminopyridine (202 mg, 1.65 mmole) and 5 ml of dichloromethane. The reaction was stirred at room temperature for 4 hours at which time the solvent was removed by rotary evaporation. The residue was suspended in ethyl acetate, and washed successively with saturated sodium bicarbonate, water and brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated in vacuo. The crude product was purified by silica gel chromatography to give 101.1.A (568 mg, 87% yield) as colorless amorphous. 1H NMR (400 MHz, CDCl3) δ ppm 8.80 (brs, 1H), 8.56 (d, J=5.8 Hz, 2H), 7.64 (d, J=6.2 Hz, 2H), 7.65-7.63 (m, 5H), 6.68 (s, 1H), 5.32 (brs, 1H), 4.52 (dd, J=14.6, 7.3 Hz, 1H), 3.95 (q, J=7.2 Hz, 2H), 3.25-3.14 (m, 2H), 1.52 (s, 9H), 1.37 (t, J=7.4 Hz, 3H)

Workup

  1. customwas removed by rotary evaporation
  2. washwashed successively with saturated sodium bicarbonate, water and brine
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-0650eb7f8f924abf9f76aa9bb0dcdc04
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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