Hydrochloric Acid → HCID 78324787, compound

HRID 2201916Notes

Reaction equation

HRID 2201916 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]([OH:25])=[O:24])=[CH:17][CH:16]=2)=[CH:11][CH:10]=1.Cl.[CH3:27]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]([O:25][CH3:27])=[O:24])=[CH:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 76286162HCID 76286162, compound

Product 1

HCID 78324787HCID 78324787, compound

Conditions

Temperature
60 °C

Procedure

To (R)-3-(4′-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)propanoic acid (14.0 mg, 0.041 mmol, see Example 1.46 for preparation) was added 1.25M hydrogen chloride in methanol (0.996 mL, 1.245 mmol). The reaction was stirred at 60° C. for 2 h. The resulting mixture was concentrated and triturated with acetonitrile to give the title compound. LCMS m/z=352.4 [M+H]+; 1H NMR (400 MHz, CD3CN) δ ppm 1.24 (d, J=6.9 Hz, 0.5H), 1.56 (d, J=6.4 Hz, 2.5H), 1.76-1.90 (m, 1H), 1.99-2.14 (m, 2H), 2.23-2.38 (m, 1H), 2.68 (t, J=7.6 Hz, 2H), 2.97 (t, J=7.6 Hz, 2H), 3.00-3.21 (m, 3H), 3.30-3.41 (m, 2H), 3.45-3.55 (m, 1H), 3.65 (s, 3H), 3.69-3.80 (m, 1H), 7.33 (d, J=8.1 Hz, 2H), 7.40 (d, J=8.2 Hz, 2H), 7.58 (d, J=8.2 Hz, 2H), 7.62 (d, J=8.2 Hz, 2H).

Workup

  1. concentrationThe resulting mixture was concentrated
  2. customtriturated with acetonitrile

Sources & evidence

ORD record
ord-34bbb312e2a84f2386e590123b1da36b
Source dataset
uspto-grants-2016_06
Patent number
US09365511B2

Reaction notes

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