Hydrochloric Acid → HCID 67820020, compound

HRID 1742937Notes

Reaction equation

HRID 1742937 reaction equation
[NH2:1][C@H:2]1[C@@H:6]([N:7]2[CH:11]=[CH:10][N:9]=[N:8]2)[CH2:5][N:4]([C:12]2[N:21]=[C:20]3[C:15]([C:16](=[O:30])[C:17]([C:25]([O:27]CC)=[O:26])=[CH:18][N:19]3[CH:22]3[CH2:24][CH2:23]3)=[CH:14][C:13]=2[F:31])[CH2:3]1.[ClH:32]>>[ClH:32].[NH2:1][C@H:2]1[C@@H:6]([N:7]2[CH:11]=[CH:10][N:9]=[N:8]2)[CH2:5][N:4]([C:12]2[N:21]=[C:20]3[C:15]([C:16](=[O:30])[C:17]([C:25]([OH:27])=[O:26])=[CH:18][N:19]3[CH:22]3[CH2:24][CH2:23]3)=[CH:14][C:13]=2[F:31])[CH2:3]1

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 67885984HCID 67885984, compound

Product 1

HCID 67820020HCID 67820020, compoundYield 85%

Procedure

Ethyl 7-[cis-3-amino-4-(1,2,3-triazol-1-yl)pyrrolidin-1-yl]-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (200 mg, 0.47 mmol) was heated with 8 ml of 6N hydrochloric acid at 110° C. for 18 hr. The solution was then evaporated to dryness and the residue was crystallized from methanol-ether to yield 160 mg (85%) of the desired hydrochloride, m.p. 240° C. (dec). 1H NMR (TFA) δ: 9.27 (s, 1H), 9.01 (s, 1H), 8.66 (s, 1H), 8.3 (d, 11.6Hz, 1H), 6.64-6.45 (m, 1H), 5.35-4.66 (m, 5H), 4.20-4.02 (m, 1H), 1.7-1.2 (m, 4H). Anal. calcd. for C18H19ClFN7O3. 1.5 H2O: C, 46.76; H, 4.80; N, 21.2; Cl, 7.67. Found: C, 46.85; H, 4.31; N, 20.62; C1, 8.36.

Workup

  1. customThe solution was then evaporated to dryness
  2. customthe residue was crystallized from methanol-ether

Sources & evidence

ORD record
ord-d89f20a3d6584b4ebc9a69f4ce1c1a1d
Source dataset
uspto-grants-1994_08
Patent number
US05342846

Reaction notes

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