Hydrochloric Acid → HCID 86759199, compound

HRID 987218Notes

Reaction equation

HRID 987218 reaction equation
C(OC([NH:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:20]2[N:15]([C:16](=[O:38])[CH:17]=[C:18]([C:23]([NH:25][CH2:26][CH:27]([NH:31][C:32]3[N:37]=[CH:36][CH:35]=[CH:34][N:33]=3)[C:28]([OH:30])=[O:29])=[O:24])[CH:19]=2)[CH:14]=1)=O)(C)(C)C.[ClH:39]>O1CCOCC1>[ClH:39].[NH2:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:22]=[CH:21][C:20]2[N:15]([C:16](=[O:38])[CH:17]=[C:18]([C:23]([NH:25][CH2:26][CH:27]([NH:31][C:32]3[N:33]=[CH:34][CH:35]=[CH:36][N:37]=3)[C:28]([OH:30])=[O:29])=[O:24])[CH:19]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22988024HCID 22988024, compound

Product 1

HCID 86759199HCID 86759199, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 3-{[7-(3-tert-butoxycarbonylamino-propoxy)-4-oxo-4H-quinolizine-2-carbonyl]-amino}-2-(pyrimidin-2-ylamino)-propionic acid (35 mg)in 4N HCl in dioxane (6 ml) was stirred for 0.5 hr at room temperature. The reaction mixture was evaporated down to dryness. NMR showed presence of small amount of starting material. The above procedure was repeated with 4N HCl in dioxane (room temperature, 45 minutes). The mixture was evaporated to dryness, triturated with ether, dissolved in water (6 ml) and lyophilized yielding pure product (XXI) (30 mg, 77%). Which was characterized by 1H NMR (400 MHz, CD3CD) δ: 8.42-8.92 (3H, broad signal with one doublet (J=2.2 Hz) in the middle), 7.90 (1H, d, J=9.6 Hz), 7.53 (!H, dd, J=2.3, 9.5 Hz), 7.34 (1H, d, J=1.3 Hz), 7.08 (1H, t, J=5.3 Hz), 6.89 (1H, d, J=1.7 Hz), 5.06 (1H, dd, J=4.2, 6.5 Hz), 4.30 (2H, t, J=5.8 Hz), 4.14 (1H, dd, J=4.2, 14.1 Hz), 3.93 (1H, dd, J=6.6, 14.1 Hz), 3.21(2H, t, J=7.2 Hz), 2.22-2.29 (2H, m).

Workup

  1. customThe reaction mixture was evaporated down to dryness
  2. customwas repeated with 4N HCl in dioxane (room temperature, 45 minutes)
  3. customThe mixture was evaporated to dryness
  4. customtriturated with ether
  5. dissolutiondissolved in water (6 ml)

Sources & evidence

ORD record
ord-634b24cc828f4649917c21d8312de65e
Source dataset
uspto-grants-2003_10
Patent number
US06630488B1

Reaction notes

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