Hydrochloric Acid → HCID 78320398, compound

HRID 2201932Notes

Reaction equation

HRID 2201932 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]([C:21]3([C:26]([OH:28])=[O:27])[CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.Cl.[CH3:30]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]([C:21]3([C:26]([O:28][CH3:30])=[O:27])[CH2:22][CH2:23][CH2:24][CH2:25]3)=[CH:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 78321671HCID 78321671, compound

Product 1

HCID 78320398HCID 78320398, compound

Procedure

To (R)-1-(4′-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)cyclopentanecarboxylic acid (30.0 mg, 0.079 mmol) was added 1.25M hydrogen chloride in methanol (1.907 mL, 2.384 mmol). The reaction was stirred at room temperature for 4 h. The mixture was concentrated and purified by HPLC to give the title compound. LCMS m/z=392.5 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.27 (d, J=6.9 Hz, 0.3H), 1.46 (d, J=6.5 Hz, 2.7H), 1.67-1.84 (m, 5H), 2.01-2.12 (m, 2H), 2.23-2.33 (m, 1H), 2.59-2.67 (m, 1H), 3.05-3.21 (m, 4H), 3.36-3.47 (m, 1H), 3.51-3.58 (m, 1H), 3.61 (s, 3H), 3.73-3.84 (m, 1H), 7.40 (d, J=8.2 Hz, 2H), 7.46 (d, J=8.3 Hz, 2H), 7.62 (d, J=8.5 Hz, 2H), 7.65 (d, J=8.3 Hz, 2H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-b8b91575547f4cf9a46a1adaf587cf74
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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