Hydrochloric Acid → HCID 131729781, compound

HRID 219990Notes

Reaction equation

HRID 219990 reaction equation
[F:1][C:2]1[CH:16]=[C:15]([C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]4[CH3:34])=[C:24]([CH2:35][O:36][CH3:37])[CH:23]=3)[O:19][N:18]=2)[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]([O:8]C(C)(C)C)=[O:7].[ClH:38]>O1CCOCC1>[ClH:38].[F:1][C:2]1[CH:16]=[C:15]([C:17]2[N:21]=[C:20]([C:22]3[CH:27]=[CH:26][C:25]([N:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH:29]4[CH3:34])=[C:24]([CH2:35][O:36][CH3:37])[CH:23]=3)[O:19][N:18]=2)[CH:14]=[CH:13][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 91114213HCID 91114213, compound

Product 1

HCID 131729781HCID 131729781, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl (2-fluoro-4-{5-[3-(methoxymethyl)-4-(2-methylpiperidin-1-yl)phenyl]-1,2,4-oxadiazol-3-yl}phenoxy)acetate (340 mg, 0.66 mmol) was dissolved in a 4M solution of HCl in dioxane (4 mL). The resulting mixture was stirred at RT for 15 hours. The precipitate was filtered off, washed with Et2O (3×) and pentane (3×), then dried under reduced pressure to give the title compound an as white powder (287 mg, 88%). 1HNMR (DMSO-d6, 300 MHz): 8.18 (brs, 1H), 8.07 (brs, 1H), 7.86 (m, 2H), 7.40 (brs, 1H), 7.30 (dd, J=8.6, 8.5 Hz, 1H), 4.91 (s, 2H), 4.58 (brs, 2H), 3.41 (s, 3H), 3.26 (m, 1H), 3.07 (m, 1H), 2.65 (m, 1H), 1.84-1.47 (m, 6H), 0.87 (brs, 3H). LC/MS (Method A): 456.3 (M+H)+; 454.4 (M−H)−. HPLC (Method A) Rt: 3.42 min (Purity: 99.7%).

Workup

  1. filtrationThe precipitate was filtered off
  2. washwashed with Et2O (3×) and pentane (3×)
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-1aaf2dc1dd574c2d852fac486d2e60c9
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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