1,2-Dichloroethane → HCID 117628496, compound

HRID 510192Notes

Reaction equation

HRID 510192 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][CH:5]=[C:4]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[C:15]([OH:17])=O)[CH:3]=1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[F:33][C:34]([F:38])([F:37])[CH2:35][NH2:36]>ClCCl>[Cl:1][C:2]1[N:7]=[N:6][CH:5]=[C:4]([NH:8][C@H:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]2[C:15]([NH:36][CH2:35][C:34]([F:38])([F:37])[F:33])=[O:17])[CH:3]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 97722,2,2-Trifluoroethylamine hydrochlorideHCID 757711-HydroxybenzotriazoleHCID 89486950HCID 89486950, compound

Product 1

HCID 117628496HCID 117628496, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

(Cis)-2-[(6-chloropyridazin-4-yl)amino]cyclohexanecarboxylic acid I-22b (2.2 g, 8.60 mmol), HOBT (2.64 g, 17.21 mmol), EDC (3.30 g, 17.21 mmol) and trifluoroethyl amine hydrochloride (2.332 g, 17.21 mmol) were added to DCM (30.0 ml) followed by the addition of TEA (6.00 ml, 43.0 mmol). The slurry was allowed to stir at RT for 17 hr. The reaction was diluted with dichloromethane washed with sat. sodium bicarb., brine dried with sodium sulfate and concentrated to an oil. Purification on Biotage Normal Phase system (DCMeOH, 0-8% B) afforded the product I-22 as a solid. (1.56 g, 51.2%).

Workup

  1. washwashed with sat. sodium bicarb
  2. dry with material, brine dried with sodium sulfate
  3. concentrationconcentrated to an oil
  4. customPurification on Biotage Normal Phase system (DCMeOH, 0-8% B)
  5. customafforded the product I-22 as a solid

Sources & evidence

ORD record
ord-249cfcbdc49142a28defca3b3395259d
Source dataset
uspto-grants-2015_08
Patent number
US09096598B2

Reaction notes

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