Diisopropylethylamine → HCID 71075406, compound

HRID 2170628Notes

Reaction equation

HRID 2170628 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][O:5][C:6]1[CH:26]=[CH:25][C:9]([CH2:10][N:11]2[C:19]3[C:14](=[CH:15][C:16]([C:20](O)=[O:21])=[CH:17][CH:18]=3)[C:13]([CH3:23])=[C:12]2[CH3:24])=[CH:8][CH:7]=1.Cl.[CH:29]1([C:32]2[CH:33]=[C:34]([C@@H:38]([NH2:40])[CH3:39])[CH:35]=[CH:36][CH:37]=2)[CH2:31][CH2:30]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.C(OCC)(=O)C>[CH:29]1([C:32]2[CH:33]=[C:34]([C@@H:38]([NH:40][C:20]([C:16]3[CH:15]=[C:14]4[C:19](=[CH:18][CH:17]=3)[N:11]([CH2:10][C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][C:3]([O:2][CH3:1])=[O:27])=[CH:26][CH:25]=3)[C:12]([CH3:24])=[C:13]4[CH3:23])=[O:21])[CH3:39])[CH:35]=[CH:36][CH:37]=2)[CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 71075337HCID 71075337, compoundHCID 86674582HCID 86674582, compound

Product 1

HCID 71075406HCID 71075406, compoundYield 102.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the 1-(4-(2-methoxy-2-oxoethoxy)benzyl)-2,3-dimethyl-1H-indole-5-carboxylic acid (50 mg, 0.14 mmol) in DCM (1 mL) was added the (S)-1-(3-cyclopropylphenyl)ethanamine hydrochloride (28 mg), DIEA (73 μL) and HATU (53 mg). The reaction mixture was allowed to stir at rt for 30 min, and then was diluted by ethyl acetate. The resulting mixture was washed with a 0.5 N HCl solution, a saturated solution of NaHCO3, and brine, dried on MgSO4, and concentrated to afford a yellow oil (73 mg) which was directly used without further purification. ESI-MS (m/z): 497 [M+H]+

Workup

  1. washThe resulting mixture was washed with a 0.5 N HCl solution
  2. dry with materiala saturated solution of NaHCO3, and brine, dried on MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-635ec30f66e24bb89e15eace0a5c1027
Source dataset
uspto-grants-2015_06
Patent number
US09051265B2

Reaction notes

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