Hydrochloric Acid → HCID 78320719, compound

HRID 2201938Notes

Reaction equation

HRID 2201938 reaction equation
[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23](O)=[O:24])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.Cl.[NH2:27][CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl>CN(C=O)C.O>[CH3:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][N:3]1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([CH2:21][CH2:22][C:23]([NH:27][CH2:28][CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:24])=[CH:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 16218890Tert-butyl 3-aminopropanoate hydrochlorideHCID 76286162HCID 76286162, compound

Product 1

HCID 78320719HCID 78320719, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-3-(4′-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)propanoic acid (30 mg, 0.089 mmol), tert-butyl 3-aminopropanoate hydrochloride (19.38 mg, 0.107 mmol), and TEA (0.037 mL, 0.267 mmol) in DMF (1 mL) was added HATU (40.6 mg, 0.107 mmol). The reaction was stirred at room temperature overnight. The mixture was added H2O (1 mL) and 1M HCl (1 mL) and purified by HPLC to give the title compound. LCMS m/z=465.5 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.27 (d, J=6.8 Hz, 0.4H), 1.44 (s, 9H), 1.46 (d, J=6.5 Hz, 2.6H), 1.69-1.82 (m, 1H), 2.02-2.12 (m, 2H), 2.23-2.32 (m, 1H), 2.35 (t, J=6.6 Hz, 2H), 2.46 (t, J=7.6 Hz, 2H), 2.93 (t, J=7.6 Hz, 2H), 3.05-3.22 (m, 4H), 3.31-3.38 (m, 2H), 3.38-3.49 (m, 1H), 3.52-3.63 (m, 1H), 3.72-3.82 (m, 1H), 6.50 (s, 1H), 7.32 (d, J=8.1 Hz, 2H), 7.39 (d, J=8.2 Hz, 2H), 7.57 (d, J=8.2 Hz, 2H), 7.63 (d, J=8.2 Hz, 2H).

Workup

  1. custompurified by HPLC

Sources & evidence

ORD record
ord-1892344c9f8b4514b6554b61d14357b5
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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