1,2-Dichloroethane → HCID 66631775, compound

HRID 714486Notes

Reaction equation

HRID 714486 reaction equation
[C:1]([C:3]1[C:4]([S:23][CH2:24][C:25]2[CH:26]=[C:27]([C:31](O)=[O:32])[CH:28]=[CH:29][CH:30]=2)=[N:5][C:6]([NH:17][CH2:18][C@@H:19]([OH:22])[CH2:20][OH:21])=[C:7]([C:15]#[N:16])[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:2].C(Cl)CCl.C1C=CC2N(O)N=[N:44]C=2C=1.[Cl-].[NH4+].C(N(CC)C(C)C)(C)C>CN(C=O)C.O1CCCC1.O>[C:1]([C:3]1[C:4]([S:23][CH2:24][C:25]2[CH:26]=[C:27]([C:31]([NH2:44])=[O:32])[CH:28]=[CH:29][CH:30]=2)=[N:5][C:6]([NH:17][CH2:18][C@@H:19]([OH:22])[CH2:20][OH:21])=[C:7]([C:15]#[N:16])[C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)#[N:2]

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 66631685HCID 66631685, compound

Product 1

HCID 66631775HCID 66631775, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

68 mg (0.15 mmol) of 3-{[(3,5-dicyano-6-{[(2R)-2,3-dihydroxypropyl]amino}-4-phenylpyridin-2-yl)sulfanyl]methyl}benzenecarboxylic acid Example 23 were dissolved in 3.4 ml of DMF. After addition of 42.5 mg (0.22 mmol) of EDC and 29.9 mg (0.22 mmol) of HOBT, the mixture was stirred at RT for 10 min. 39.5 mg (0.74 mmol) of ammonium chloride and 133.6 mg (1.03 mmol) of N,N-diisopropylethylamine were added, and the reaction mixture was stirred at RT overnight. Water and tetrahydrofuran were added to the reaction mixture until a clear solution had formed. The solution was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid).

Workup

  1. stirringthe reaction mixture was stirred at RT overnight
  2. customhad formed
  3. customThe solution was purified by preparative HPLC (Chromasil, water/acetonitrile+0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-43f16369431a43539535d9f6d0298642
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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