Hydrochloric Acid → HCID 67497224, compound

HRID 1628342Notes

Reaction equation

HRID 1628342 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:10]([NH:12][C:13]2[N:17]([CH3:18])[N:16]=[C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH:14]=2)=[O:11])=[CH:4][CH:3]=1.[ClH:32]>O1CCOCC1>[ClH:32].[ClH:32].[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:10]([NH:12][C:13]2[N:17]([CH3:18])[N:16]=[C:15]([C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH:14]=2)=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67496386HCID 67496386, compound

Product 1

HCID 67497224HCID 67497224, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a 25 ml flask was added ethyl 2-((S)-3-(4-fluorophenyl)-1-(1-methyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxopropan-2-ylamino)acetate 103.1.C (199 mg, 0.47 mmole) and 1 ml of 1,4-dioxane. To the solution, 1 ml of 4N-hydrogen chloride solution in 1,4-dioxane (4 mmol) was added at 0° C. After then, the solvent was removed by rotary evaporation. The crude product was dried under a high vacuum to give 103.1 (221 mg, 95% yield) as colorless amorphous. LCMS ESI (pos.) m/e: 426 (M+H): 1H NMR (400 MHz, DMSO-d6) δ ppm 11.5 (brs, 1H), 8.86 (d, J=7.0 Hz, 2H), 8.33 (d, J=6.7 Hz, 2H), 7.42 (dd, J=8.6, 5.4 Hz, 2H), 7.20 (t, J=8.8 Hz, 2H), 7.15 (s, 1H), 4.65 (t, J=7.2 Hz, 1H), 4.01 (s, 2H), 3.74 (s, 3H), 3.62 (brs, 1H), 3.44 (q, J=7.0 Hz, 2H), 3.41 (dd, J=12.1, 6.6 Hz, 1H), 3.26 (dd, J=13.7, 8.6 Hz, 1H), 1.06 (t, J=6.8 Hz, 3H).

Workup

  1. customAfter then, the solvent was removed by rotary evaporation
  2. dry with materialThe crude product was dried under a high vacuum

Sources & evidence

ORD record
ord-760d952ee9024a83a5703bec3bf77346
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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