1,2-Dichloroethane → HCID 89495412, compound

HRID 510190Notes

Reaction equation

HRID 510190 reaction equation
Cl.Cl.[Cl:3][C:4]1[N:9]=[N:8][CH:7]=[C:6]([NH:10][C:11]([CH3:16])([CH3:15])[C:12]([OH:14])=O)[CH:5]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[F:32][C:33]([F:37])([F:36])[CH2:34][NH2:35]>C(Cl)Cl>[Cl:3][C:4]1[N:9]=[N:8][CH:7]=[C:6]([NH:10][C:11]([CH3:16])([CH3:15])[C:12]([NH:35][CH2:34][C:33]([F:37])([F:36])[F:32])=[O:14])[CH:5]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 117629129HCID 117629129, compound

Product 1

HCID 89495412HCID 89495412, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-[(6-chloropyridazin-4-yl)amino]-2-methylpropanoic acid dihydrochloride I-21b (1.23 g, 4.26 mmol), HOBT (0.979 g, 6.39 mmol), EDC (1.226 g, 6.39 mmol), and trifluoroethyl amine hydrochloride (0.866 g, 6.39 mmol) were added to DCM (20.0 ml) followed by the addition of TEA (29.7 ml, 213 mmol). The reaction was allowed to stir at room temperature for 17 hrs. The reaction was then diluted with DCM, washed with saturated sodium bicarbonate, brine, dried with sodium sulfate and concentrated in vacuo to an oil. Purification on Biotage Normal Phase system (DCM:MeOH, 0-8% B) to afford the product I-21 as a solid. The solid was dried under vacuum (295 mg, 22.3%). LRMS (ESI) m/z 297.0 [(M+H)+; calcd for C10H12ClF3N4O: 297.0].

Workup

  1. washwashed with saturated sodium bicarbonate, brine
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated in vacuo to an oil
  4. customPurification on Biotage Normal Phase system (DCM:MeOH, 0-8% B)
  5. customto afford the product I-21 as a solid
  6. customThe solid was dried under vacuum (295 mg, 22.3%)

Sources & evidence

ORD record
ord-724d9e2d9538482a97731fd31fe4670d
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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