Hydrochloric Acid → HCID 69997281, compound

HRID 963440Notes

Reaction equation

HRID 963440 reaction equation
[ClH:1].[CH:2]1([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:40])=[C:15]([C:19]#[C:20][C:21]4[CH:26]=[C:25]([CH2:27][C:28]5[C:29]([NH2:35])=[N:30][C:31]([NH2:34])=[N:32][CH:33]=5)[CH:24]=[C:23]([O:36][CH3:37])[C:22]=4[O:38][CH3:39])[C:16]=3F)[C:11](=[O:41])[C:10]([C:42]([OH:44])=[O:43])=[CH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-:45].[Na+].Cl.[CH3:48]O>>[ClH:1].[CH:2]1([N:8]2[C:17]3[C:12](=[CH:13][C:14]([F:40])=[C:15]([C:19]#[C:20][C:21]4[CH:26]=[C:25]([CH2:27][C:28]5[C:29]([NH2:35])=[N:30][C:31]([NH2:34])=[N:32][CH:33]=5)[CH:24]=[C:23]([O:36][CH3:37])[C:22]=4[O:38][CH3:39])[C:16]=3[O:45][CH3:48])[C:11](=[O:41])[C:10]([C:42]([OH:44])=[O:43])=[CH:9]2)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 69996673HCID 69996673, compound

Product 1

HCID 69997281HCID 69997281, compoundYield 78%

Procedure

16ar) A suspension of 0.33 g of 1-cyclohexyl-7-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3-dimethoxy-phenylethynyl]-6,8-difluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid hydrochloride (Example 16aq)) in 5 ml of methanol is treated with 2 ml of 28% aqueous sodium hydroxide solution and held at reflux for 5 hrs. The beige suspension is cooled to room temperature and acidified with 25% aqueous hydrochloric acid. The precipitated substance is filtered off under suction, washed with 10 ml of water, 10 ml of ethanol and 10 ml of ether and dried. 0.264 g (78%) of 1-cyclohexyl-7-[5-(2,4-diamino-pyrimidin-5-ylmethyl)-2,3- dimethoxy-phenylethynyl]-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid hydrochloride is obtained as a beige solid. Yield: 78%. M.p.>205° (dec.). Mass spectrum (FAB): peaks inter alia at 602 (M++H, 100%), 588 (10%), 520 (7%).

Workup

  1. temperatureat reflux for 5 hrs
  2. filtrationThe precipitated substance is filtered off under suction
  3. washwashed with 10 ml of water, 10 ml of ethanol and 10 ml of ether
  4. customdried

Sources & evidence

ORD record
ord-fb41c55d3a844be9af5ef3074ca4c7e3
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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