Hydrochloric Acid → HCID 46869362, compound

HRID 1628343Notes

Reaction equation

HRID 1628343 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]CC)=[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.O.[OH-].[Li+].O.Cl>O1CCCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:25][CH2:26][C:27]([OH:29])=[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67496386HCID 67496386, compound

Product 1

HCID 46869362HCID 46869362, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

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 (331 mg, 0.78 mmole), lithium hydroxide monohydrate (65.3 mg, 1.56 mmole), 1 ml of water and 6 ml of tetrahydrofuran. After 3 hours, 0.78 ml of 2N-hydrogen chloride solution was added to neutralize. The solvent was removed by rotary evaporation. The crude product was purified by silica gel chromatography to give 103.2 (268 mg, 87% yield) as colorless amorphous. LCMS ESI (pos.) m/e: 398 (M+H); 1H NMR (400 MHz, DMSO-d6) δ ppm 8.57 (d, J=5.5 Hz, 2H), 7.72 (d, J=6.3 Hz, 2H), 7.33 (dd, J=8.4, 5.7 Hz, 2H), 7.13 (t, J=8.8 Hz, 2H), 6.81 (s, 1H), 3.66 (s, 3H), 3.58 (t, J=6.8 Hz, 1H), 3.21 (d, J=16.9 Hz, 1H), 3.11 (d, J=17.2 Hz, 1H), 3.02 (dd, J=13.6, 5.9 Hz, 1H), 2.89 (dd, J=13.6, 7.9 Hz, 1H).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customThe crude product was purified by silica gel chromatography

Sources & evidence

ORD record
ord-c297faf724bf4cc89f9f887f4b59369d
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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