1,2-Dichloroethane → HCID 136106406, compound

HRID 470365Notes

Reaction equation

HRID 470365 reaction equation
CCN(CC)CC.[Cl-].[C:9]([C:12]1[C:39]([F:40])=[CH:38][C:15]2[NH:16][C:17]([C:19]3[CH:20]=[C:21]([C:26]4[C:27]([O:32][CH2:33][CH2:34][NH+:35]([CH3:37])[CH3:36])=[N:28][CH:29]=[CH:30][CH:31]=4)[CH:22]=[CH:23][C:24]=3[OH:25])=[N:18][C:14]=2[CH:13]=1)(O)=[O:10].[NH2:41][CH2:42][CH2:43][C:44]1[N:48]=[CH:47][NH:46][CH:45]=1.C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C>[CH3:37][N:35]([CH3:36])[CH2:34][CH2:33][O:32][C:27]1[C:26]([C:21]2[CH:22]=[CH:23][C:24]([OH:25])=[C:19]([C:17]3[NH:16][C:15]4[CH:38]=[C:39]([F:40])[C:12]([C:9]([NH:41][CH2:42][CH2:43][C:44]5[NH:48][CH:47]=[N:46][CH:45]=5)=[O:10])=[CH:13][C:14]=4[N:18]=3)[CH:20]=2)=[CH:31][CH:30]=[CH:29][N:28]=1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 136339726HCID 136339726, compoundHCID 178419017HCID 178419017, compound

Product 1

HCID 136106406HCID 136106406, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Et3N (0.079 mL, 0.568 mmol, 8.0 eq.) was added to a mixture containing the crude carboxylic acid salt 9c (0.071 mmol, 1.0 eq.), histamine.2HCl (16 mg, 0.085 mmol, 1.2 eq.), EDC (15 mg, 0.078 mmol, 1.1 eq.) and HOBt (11 mg, 0.078 mmol, 1.1 eq.) in dry DMF (2 mL) and stirred for 16 h. The reaction mixture was concentrated in vacuo and the residue was purified by flash chromatography [10% (5% aq NH4OH/MeOH)/DCM] to afford the title compound (Rf=0.40) as a light yellow powder (20.1 mg, 53%). ES-MS MH+ 530.30.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue was purified by flash chromatography [10% (5% aq NH4OH/MeOH)/DCM]

Sources & evidence

ORD record
ord-e6d6cee215d546ad86e63a56ef1b0588
Source dataset
uspto-grants-2014_01
Patent number
US08629147B2

Reaction notes

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