Triethylamine → HCID 178519258, compound

HRID 538060Notes

Reaction equation

HRID 538060 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][CH2:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([C:17]([N:19]2[CH2:24][CH2:23][N:22]([C:25]([CH:27]3[CH2:29][CH2:28]3)=[O:26])[CH2:21][CH2:20]2)=[O:18])[CH2:13][CH2:12]1.C(N(CC)CC)C.Cl[C:38](Cl)([O:40]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[NH:1][C:38](=[O:40])[N:9]([CH2:10][C@H:11]3[CH2:12][CH2:13][C@H:14]([C:17]([N:19]4[CH2:24][CH2:23][N:22]([C:25]([CH:27]5[CH2:29][CH2:28]5)=[O:26])[CH2:21][CH2:20]4)=[O:18])[CH2:15][CH2:16]3)[C:3]=2[CH:4]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 94429TriphosgeneHCID 178507591HCID 178507591, compound

Product 1

HCID 178519258HCID 178519258, compoundYield 147.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of {trans-4-[(2-Amino-5-chloro-phenylamino)-methyl]-cyclohexyl}-(4-cyclopropane carbonyl-piperazin-1-yl)-methanone (448 mg, 1.07 mmol), triethylamine (0.45 mL, 3.22 mmol) in DCM (10 mL) was cooled at 0° C. Triphosgene (104 mg, 0.35 mmol) was added and the reaction was allowed to warm up to room temperature and left stirring for 18 hours. The reaction was diluted with 0.4 M Na2CO3 solution, the organic phase collected and the solvent removed under reduced pressure. The crude product was purified by SiO2 column eluting with ethylacectate-methanol (9:1), affording 230 mg of the pure product (49% yield).

Workup

  1. waitleft
  2. customthe organic phase collected
  3. customthe solvent removed under reduced pressure
  4. customThe crude product was purified by SiO2 column
  5. washeluting with ethylacectate-methanol (9:1)

Sources & evidence

ORD record
ord-8350ad6c22024d08a78a2cf6b2e78f68
Source dataset
uspto-grants-2014_10
Patent number
US08865704B2

Reaction notes

Loading…