Hydrochloric Acid → HCID 69954724, compound

HRID 1978918Notes

Reaction equation

HRID 1978918 reaction equation
[NH2:1][C:2]1[N:3]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][N:12]([N:21]3[C:30](=[O:31])[C:29]4[C:24](=[CH:25][C:26]([C:32]([O:34]C)=[O:33])=[CH:27][CH:28]=4)[N:23]=[C:22]3[CH3:36])[C:11](=[O:37])[C:5]3=[CH:6][CH2:7][CH2:8][C:9]([CH:10]=1)=[C:4]23.C1COCC1.[OH-].[K+].Cl>O.C(Cl)Cl.CO>[NH2:1][C:2]1[N:3]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:13][N:12]([N:21]3[C:30](=[O:31])[C:29]4[C:24](=[CH:25][C:26]([C:32]([OH:34])=[O:33])=[CH:27][CH:28]=4)[N:23]=[C:22]3[CH3:36])[C:11](=[O:37])[C:5]3=[CH:6][CH2:7][CH2:8][C:9]([CH:10]=1)=[C:4]23

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 69956107HCID 69956107, compound

Product 1

HCID 69954724HCID 69954724, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Conditions

Temperature
22.5 °C

Procedure

0.6 g (1.22 mmmol) of the product of Example 28A and 30 ml of THF are introduced into a reactor. After solubilization, a solution of 0.135 g of KOH in 8 ml of water is added and the mixture is kept stirring for 3 h at 20-25° C. The mixture is neutralized with 0.1 N HCl to pH 6.8 and the THF is evaporated off at 50° C. under a vacuum of 20 rnm Hg. The residue is chromatographed, eluting with CH2Cl2 progressively enriched with methanol. The product obtained is crystallized from 10 ml of CH2Cl2 and the precipitate is filtered off. 0.25 g is obtained (Yld=42.7%). M.p.>275° C.—TLC (85/15 CH2Cl2/MeOH): Rf=0.35.

Workup

  1. customthe THF is evaporated off at 50° C. under a vacuum of 20 rnm Hg
  2. customThe residue is chromatographed
  3. washeluting with CH2Cl2
  4. customThe product obtained
  5. customis crystallized from 10 ml of CH2Cl2
  6. filtrationthe precipitate is filtered off
  7. custom0.25 g is obtained (Yld=42.7%)

Sources & evidence

ORD record
ord-78618c1aa24641c28410d2dd7159f590
Source dataset
uspto-grants-2001_05
Patent number
US06239130B1

Reaction notes

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