Hydrochloric Acid → HCID 78320399, compound

HRID 2201933Notes

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.[NH2:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29].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:20]=[CH:19][C:18]([CH2:21][CH2:22][C:23]([NH:26][CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[O:24])=[CH:17][CH:16]=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), tert-butyl 2-aminoacetate (18.66 mg, 0.142 mmol), and TEA (0.033 mL, 0.237 mmol) in DMF (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=451.4 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.27 (d, J=6.9 Hz, 0.4H), 1.45 (s, 9H), 1.47 (d, J=6.5 Hz, 2.6H), 1.71-1.83 (m, 1H), 2.02-2.12 (m, 2H), 2.23-2.33 (m, 1H), 2.55 (t, J=7.5 Hz, 2H), 2.96 (t, J=7.8 Hz, 2H), 3.06-3.21 (m, 4H), 3.37-3.47 (m, 1H), 3.50-3.63 (m, 1H), 3.72-3.84 (m, 1H), 6.63 (s, 1H), 7.35 (d, J=8.2 Hz, 2H), 7.39 (d, J=8.2 Hz, 2H), 7.58 (d, J=8.2 Hz, 2H), 7.64 (d, J=8.2 Hz, 2H).

Workup

custompurified by HPLC

Sources & evidence

ORD record: ord-e054810031bb4026975289a594d6cbe1
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365511B2

Reaction notes

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