Hydrochloric Acid → HCID 67497038, compound

HRID 1628248Notes

Reaction equation

HRID 1628248 reaction equation
[CH3:1][N:2]1[C:6]([NH:7][C:8](=[O:22])[C@@H:9]([NH:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][C:4]([C:23]2[CH:28]=[CH:27][N:26]=[CH:25][CH:24]=2)=[N:3]1.[ClH:29]>O.O1CCOCC1>[ClH:29].[ClH:29].[CH3:1][N:2]1[C:6]([NH:7][C:8](=[O:22])[C@@H:9]([NH:17][CH2:18][C:19]([OH:21])=[O:20])[CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[CH:5][C:4]([C:23]2[CH:24]=[CH:25][N:26]=[CH:27][CH:28]=2)=[N:3]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67496729HCID 67496729, compound

Product 1

HCID 67497038HCID 67497038, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a 200 ml flask was added 640 mg of (S)-2-(1-(1-methyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylamino)acetic acid diTFA, 20 ml of dioxane, 20 drops of water and then slowly 3 ml of hydrogen chloride (2.0 M in diethyl ether). The solvent was then removed using a rotary evaporator and placed under high vacuum to give 565 mg (S)-2-(1-(1-methyl-3-(pyridin-4-yl)-1H-pyrazol-5-ylamino)-1-oxo-3-phenylpropan-2-ylamino)acetic acid dihydrochloride as an off white solid. The product was redissolved in 10% MeOH in DCM and the solvent was then removed using a rotary evaporator and placed under high vacuum to give 505 mg of 17.8 as a white solid. MS ESI (pos.) m/e: 380.2 (M+H); 1H NMR (400 MHz, CD3OD) δ ppm 8.52 (d, J=6.50 Hz, 2H), 7.72-7.89 (m, 2H), 7.25-7.47 (m, 5H), 6.65-6.81 (m, 1H), 4.17 (dd, J=8.80, 6.46 Hz, 1H), 3.51-3.57 (m, 4H), 3.41-3.51 (m, 1H), 3.28 (d, J=6.26 Hz, 1H), 3.10-3.23 (m, 1H).

Workup

  1. customThe solvent was then removed
  2. customa rotary evaporator

Sources & evidence

ORD record
ord-aae99d6419ee4f989dc338ca9fc04cf5
Source dataset
uspto-grants-2014_07
Patent number
US08785468B2

Reaction notes

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