1,2-Dichloroethane → HCID 66631434, compound

HRID 714479Notes

Reaction equation

HRID 714479 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([S:8][C@H:9]([C:11]2[CH:12]=[C:13]([C:17]([OH:19])=O)[CH:14]=[CH:15][CH:16]=2)[CH3:10])[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][OH:31])=[CH:24][CH:23]=2)[C:3]=1[C:32]#[N:33].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>[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH:9]([C:11]2[CH:12]=[C:13]([C:17]([NH2:44])=[O:19])[CH:14]=[CH:15][CH:16]=2)[CH3:10])[C:5]([C:20]#[N:21])=[C:4]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][OH:31])=[CH:26][CH:27]=2)[C:3]=1[C:32]#[N:33]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 56592009HCID 56592009, compound

Product 1

HCID 66631434HCID 66631434, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

33 mg (0.072 mmol) of rac-3-[(1S)-1-({6-amino-3,5-dicyano-4-[4-(2-hydroxyethoxy)phenyl]-pyridin-2yl}sulfanyl)ethyl]benzenecarboxylic acid Example 16 were initially charged in 1.6 ml of DMF. After addition of 20.6 mg (0.107 mmol) of EDC and 14.5 mg (0.107 mmol) of HOBT, the mixture was stirred at RT for 10 min. 19.2 mg (0.358 mmol) of ammonium chloride and 64.8 mg (0.502 mmol) of N,N-diisopropylethylamine were then added, and the reaction solution was stirred at RT overnight. The reaction solution was purified by preparative HPLC (Chromasil, water/acetonitrile).

Workup

  1. stirringthe reaction solution was stirred at RT overnight
  2. customThe reaction solution was purified by preparative HPLC (Chromasil, water/acetonitrile)

Sources & evidence

ORD record
ord-c58341dc76614bdea8eb06f47b1dfa2e
Source dataset
uspto-grants-2015_11
Patent number
US09187428B2

Reaction notes

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