1,2-Dichloroethane → HCID 58408408, compound

HRID 1948567Notes

Reaction equation

HRID 1948567 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:17]3[CH:22]=[N:21][CH:20]=[CH:19][N:18]=3)=[C:12]([CH:16]=2)[C:13]([OH:15])=[O:14])[CH:5]=[N:6][CH:7]=1.[CH2:23](Cl)[CH2:24]Cl.C1C=CC2N(O)N=NC=2C=1.ClC1C=C(CN)C=CC=1OC.CN1CCOCC1>CN(C=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[CH:9]=[CH:10][C:11]([C:17]3[CH:22]=[N:21][CH:20]=[CH:19][N:18]=3)=[C:12]([CH:16]=2)[C:13]([O:15][CH2:23][CH3:24])=[O:14])[CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 7380383-Chloro-4-methoxybenzylamineHCID 58408410HCID 58408410, compound

Product 1

HCID 58408408HCID 58408408, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of the carboxylic acid (3-4, 0.062 g, 0.186 mmol, 1 equiv), EDC (0.053 g, 0.279 mmol, 1.5 equiv), and HOBt (0.045 g, 0.297 mmol, 1.6 equiv) in DMF (1 mL), 1-(3-chloro-4-methoxyphenyl)methanamine (0.045 g, 0.260 mmol, 1.4 equiv) was added followed by N-methylmorpholine (0.102 mL, 0.929 mmol, 5 equiv) and the reaction was stirred overnight at room temperature The reaction mixture was filtered and put on a reverse phase preparative HPLC system running acetonitrile/water with a TFA buffer (5 to 75% CH3CN in water). The cleanest fractions were pooled, concentrated and freebased to afford the product (3-5) as a white solid. Data for H-1: HRMS [M+H] C25H21ClN4O2 calc'd 445.1426. found 445.1439.

Workup

  1. additionwas added
  2. filtrationwas filtered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-ea868f74b2214210a79bfa52328b2269
Source dataset
uspto-grants-2013_03
Patent number
US08399494B2

Reaction notes

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