1,2-Dichloroethane → HCID 87160530, compound

HRID 574160Notes

Reaction equation

HRID 574160 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:18])([F:17])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]([NH:24][C@H:25]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:44])[F:43])[CH:37]=3)[CH2:26][C:27]([NH:29][C:30]([CH3:35])([C:32]([OH:34])=O)[CH3:31])=[O:28])=[O:23])[N:9]=2)=[CH:4][CH:3]=1.C(Cl)CCl.C1C=CC2N(O)N=[N:56]C=2C=1.N>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]([CH2:13][C@H:14]([OH:19])[C:15]([F:17])([F:18])[F:16])[C:11](=[O:20])[N:10]([CH2:21][C:22]([NH:24][C@H:25]([C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42]([F:45])([F:43])[F:44])[CH:37]=3)[CH2:26][C:27]([NH:29][C:30]([CH3:35])([C:32]([NH2:56])=[O:34])[CH3:31])=[O:28])=[O:23])[N:9]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 222AmmoniaHCID 757711-HydroxybenzotriazoleHCID 87160602HCID 87160602, compound

Product 1

HCID 87160530HCID 87160530, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 50 mg (75 μmol) of the compound of Example 39, 29 mg (0.15 mmol) of EDC and 20 mg (0.15 mmol) of HOBt in 2 ml of DMF was stirred at RT for 20 min and then poured into 5 ml of ammonia (35% strength solution in water). The reaction mixture was stirred at RT for 30 min and then concentrated on a rotary evaporator, acidified with 2.5 N hydrochloric acid and separated by preparative HPLC [Method 6]. The appropriate fraction was concentrated on a rotary evaporator and the residue was dried under high vacuum. This gave 42 mg (84% of theory) of the title compound.

Workup

  1. stirringThe reaction mixture was stirred at RT for 30 min
  2. concentrationconcentrated on a rotary evaporator
  3. customseparated by preparative HPLC [Method 6]
  4. concentrationThe appropriate fraction was concentrated on a rotary evaporator
  5. customthe residue was dried under high vacuum

Sources & evidence

ORD record
ord-5180202c136a4ddaa5685c0233531fea
Source dataset
uspto-grants-2015_05
Patent number
US09034855B2

Reaction notes

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