Hydrochloric Acid → HCID 78321036, compound

HRID 2201942Notes

Reaction equation

HRID 2201942 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.[NH:26]1[CH2:31][CH2:30][CH:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:28][CH2:27]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl>CN(C=O)C>[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]([N:26]3[CH2:31][CH2:30][CH:29]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH2:28][CH2:27]3)=[O:24])=[CH:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 70770Ethyl 4-piperidinecarboxylateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 76286162HCID 76286162, compound

Product 1

HCID 78321036HCID 78321036, compound

Reagents, catalysts & solvents 1

HCID 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), ethyl piperidine-4-carboxylate (16.77 mg, 0.107 mmol), and TEA (0.025 mL, 0.178 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 1M HCl (2 mL) and purified by HPLC to give the title compound. LCMS m/z=477.5 [M+H]+; 1.19 (t, J=7.1 Hz, 3H), 1.25 (d, J=6.8 Hz, 0.3H), 1.37-1.50 (m, 2H), 1.44 (d, J=6.7 Hz, 2.7H), 1.67-1.77 (m, 1H), 1.77-1.89 (m, 2H), 1.99-2.09 (m, 2H), 2.20-2.31 (m, 1H), 2.45-2.56 (m, 1H), 2.57-2.79 (m, 3H), 2.92 (t, J=6.6 Hz, 2H), 3.00-3.19 (m, 5H), 3.34-3.47 (m, 1H), 3.50-3.59 (m, 1H), 3.70-3.86 (m, 2H), 4.06 (q, J=7.0 Hz, 2H), 3.70-3.86 (m, 2H), 7.32 (d, J=8.1 Hz, 2H), 7.36 (d, J=8.2 Hz, 2H), 7.54 (d, J=8.2 Hz, 2H), 7.60 (d, J=8.2 Hz, 2H).

Workup

  1. custompurified by HPLC

Sources & evidence

ORD record
ord-b20404c6722b46c3a3daf8e3e4f97e4b
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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