1,2-Dichloroethane → HCID 178457733, compound

HRID 2059743Notes

Reaction equation

HRID 2059743 reaction equation
[OH:1][C:2]1[C:7]([C:8]([NH:10][C:11]([CH3:16])([C:13]([OH:15])=O)[CH3:12])=[O:9])=[CH:6][N:5]=[C:4]([N:17]2[CH:21]=[CH:20][CH:19]=[N:18]2)[N:3]=1.CCN(C(C)C)C(C)C.[NH:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C.CCOC(C)=O>[N:31]1([C:13](=[O:15])[C:11]([NH:10][C:8]([C:7]2[C:2]([OH:1])=[N:3][C:4]([N:17]3[CH:21]=[CH:20][CH:19]=[N:18]3)=[N:5][CH:6]=2)=[O:9])([CH3:12])[CH3:16])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:33][CH2:32]1

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 10328IndolineHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 178457734HCID 178457734, compound

Product 1

HCID 178457733HCID 178457733, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the product of Example 188 (100 mg, 0.343 mmol), DIPEA (0.15 mL 0.86 mmol), 2,3-dihydro-1H-indole (0.04 ml, 0.36 mmol) and HOBt (55.2 mg, 0.36 mmol) in 1.4 mL DMF was added EDC (69.1 mg, 0.36 mmol). The reaction aged at rt for 3.5 h. The reaction was diluted with EtOAc and washed with aq HCl (2 M) and water. The organic portion was partially concentrated and the product was allowed to crystallize. The mixture was diluted with 80% EtOAc/20% hexane before the product was isolated by filtration. It was then washed with 80% EtOAc/20% hexane to afford the title compound. HPLC/MS: 393.0 (M+1); Rt=2.63 min.

Workup

  1. washwashed with aq HCl (2 M) and water
  2. concentrationThe organic portion was partially concentrated
  3. customto crystallize
  4. additionThe mixture was diluted with 80% EtOAc/20% hexane before the product
  5. customwas isolated by filtration
  6. washIt was then washed with 80% EtOAc/20% hexane

Sources & evidence

ORD record
ord-caec6ed863494649af7c253550884945
Source dataset
uspto-grants-2012_10
Patent number
US08278304B2

Reaction notes

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