Hydrochloric Acid → HCID 68907622, compound

HRID 446075Notes

Reaction equation

[NH2:1][C:2]1([CH3:30])[C:6]2([CH2:8][CH2:7]2)[CH2:5][N:4]([C:9]2[C:18]([O:19][CH3:20])=[C:17]3[C:12]([C:13](=[O:28])[C:14]([C:25]([OH:27])=[O:26])=[CH:15][N:16]3[C@@H:21]3[CH2:23][C@@H:22]3[F:24])=[CH:11][C:10]=2[F:29])[CH2:3]1.[ClH:31].C(O)(C)C>CO>[ClH:31].[NH2:1][C:2]1([CH3:30])[C:6]2([CH2:7][CH2:8]2)[CH2:5][N:4]([C:9]2[C:18]([O:19][CH3:20])=[C:17]3[C:12]([C:13](=[O:28])[C:14]([C:25]([OH:27])=[O:26])=[CH:15][N:16]3[C@@H:21]3[CH2:23][C@@H:22]3[F:24])=[CH:11][C:10]=2[F:29])[CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

7-[7-amino-7-methyl-5-azaspiro[2.4]heptan-5-yl]-6-fluoro-1-[(1R,2S)-2-fluorocyclopropyl]-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid in which configuration of the amino group in the substituent at position 7 is the same as the one produced in Example 9 (18.07 g, 39.4 mmol) was suspended in methanol (54 mL), and 1N hydrochloric acid (43.4 mL, 43.4 mmol) was added to the suspension at room temperature. Isopropyl alcohol (180 mL) was then added, and the mixture was stirred in a water bath at 50° C. for some time until precipitated gummy material thoughly turned to crystal. After allowing to stand at room temperature for 1 hour, the crystals were collected by filtration, and washed with a small amount of isopropyl alcohol (twice). The crystals were then dried under reduced pressure to obtain the title compound 12.91 g (27.2 mmol, 69%) as a yellow powder.

Workup

customuntil precipitated gummy material
filtrationthe crystals were collected by filtration
washwashed with a small amount of isopropyl alcohol (twice)
customThe crystals were then dried under reduced pressure

Sources & evidence

ORD record: ord-33580a7cd2274fbfaeb49c93dc732e18
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476429B2

Reaction notes

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