Ethylamine hydrochloride → HCID 54759258, compound

HRID 1526680Notes

Reaction equation

HRID 1526680 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:17]=[CH:18][C:13]=3[N:12]3[C:25]([CH3:28])=[N:26][N:27]=[C:11]3[C@H:10]([CH2:29][C:30](O)=[O:31])[N:9]=2)=[CH:4][CH:3]=1.[CH3:33][CH2:34][N:35](C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.C(N)C>CN(C=O)C.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:14]3[CH:15]=[C:16]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:17]=[CH:18][C:13]=3[N:12]3[C:25]([CH3:28])=[N:26][N:27]=[C:11]3[C@H:10]([CH2:29][C:30]([NH:35][CH2:34][CH3:33])=[O:31])[N:9]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 11198Ethylamine hydrochlorideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 68003876HCID 68003876, compound

Product 1

HCID 54759258HCID 54759258, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

[(4S)-6-(4-Chlorophenyl)-1-methyl-8-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]acetic acid (for a preparation see Intermediate 1) (29 mg) was dissolved in DMF (2 ml). DIPEA (23 μl), HATU (29.9 mg) and ethylamine hydrochloride (10.68 mg) were added to the reaction mixture. The reaction was stirred at room temperature overnight. The mixture was dissolved in ethyl acetate (10 ml) and washed with saturated hydrogen carbonate solution (5 ml). The organic phase was washed with water (5 ml) and brine (5 ml). The organic layer was dried and the solvent evaporated. The residue was chromatographed (0-5% methanol:DCM) and then further purified by MDAP (formate modifier) to give 2-[(4S)-6-(4-chlorophenyl)-1-methyl-8-phenyl-4H-[1,2,4]triazolo[4,3-a][1,4]benzodiazepin-4-yl]-N-ethylacetamide (7.5 mg) as a white oil. LCMS (formate): MH+ 470/472, RT 1.10 min

Workup

  1. washwashed with saturated hydrogen carbonate solution (5 ml)
  2. washThe organic phase was washed with water (5 ml) and brine (5 ml)
  3. customThe organic layer was dried
  4. customthe solvent evaporated
  5. customThe residue was chromatographed (0-5% methanol:DCM)
  6. customfurther purified by MDAP (formate modifier)

Sources & evidence

ORD record
ord-56536d1b660c41719129c0b36c6ce0eb
Source dataset
uspto-grants-2015_07
Patent number
US09085582B2

Reaction notes

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