Hydrochloric Acid → HCID 78320092, compound

HRID 2201920Notes

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][C@@H:28]([CH3:36])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl>O1CCCC1.C(#N)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]([NH:27][C@@H:28]([CH3:36])[C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:24])=[CH:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of (R)-3-(4′-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)propanoic acid (40 mg, 0.119 mmol), (S)-tert-butyl 2-aminopropanoate hydrochloride (25.8 mg, 0.142 mmol), and TEA (0.050 mL, 0.356 mmol) in tetrahydrofuran (1 mL) and acetonitrile (1 mL) was added HATU (54.1 mg, 0.142 mmol). The reaction was stirred at 60° C. for 2 h. The mixture was added 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=6.7 Hz, 0.4H), 1.28 (d, J=7.2 Hz, 3H), 1.44 (s, 9H), 1.46 (d, J=6.6 Hz, 2.6H), 1.70-1.82 (m, 1H), 2.01-2.12 (m, 2H), 2.23-2.33 (m, 1H), 2.51 (t, J=7.8 Hz, 2H), 2.95 (t, J=7.7 Hz, 2H), 3.05-3.21 (m, 4H), 3.37-3.48 (m, 1H), 3.49-3.62 (m, 1H), 3.73-3.83 (m, 1H), 4.20-4.29 (m, 1H), 6.64 (d, 7.1 Hz, 1H), 7.34 (d, J=8.1 Hz, 2H), 7.39 (d, J=8.1 Hz, 2H), 7.58 (d, J=8.1 Hz, 2H), 7.63 (d, J=8.1 Hz, 2H).

Workup

custompurified by HPLC

Sources & evidence

ORD record: ord-2905495ec05d46e4b9bfef3ae0d9e6c2
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365511B2

Reaction notes

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