Hydrochloric Acid → HCID 178470786, compound

HRID 1056852Notes

Reaction equation

HRID 1056852 reaction equation
C(O[C:4]([C:6]1[C:7]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:8]=2[S:9][C:10]=1[NH2:11])=[O:5])C.[C:17]([CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])#[N:18].Cl>O1CCOCC1>[CH2:23]([O:22][C:20](=[O:21])[CH2:19][C:17]1[N:18]=[C:4]([OH:5])[C:6]2[C:7]3[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][C:8]=3[S:9][C:10]=2[N:11]=1)[CH3:24]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7764Ethyl cyanoacetateHCID 292644Ethyl 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylate

Product 1

HCID 178470786HCID 178470786, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of 2-amino-5,6,7,8-tetrahydro-4H-cyclohepta[b]thiophene-3-carboxylic acid ethyl ester (7 g, 0.02928 mol) and ethyl cyanoacetate (6.5 g, 0.05857 mol) in 72 ml of 1,4-dioxane was saturated with HCl gas while cooling the mixture. The mixture was stirred for 18 h at ambient temperature, then quenched with solid NaHCO3, diluted with 100 ml water and extracted with ethyl acetate (100 ml×3). The organic layer was separated, dried over Na2SO4 and concentrated under vacuum. The crude solid was triturated with diethyl ether (100 ml) to give (4-hydroxy-6,7,8,9-tetrahydro-5H-10-thia-1,3-diaza-benz[a]azulen-2-yl)-acetic acid ethyl ester (5.5 g, 62%) as a pale yellow solid. 1H NMR (400 MHz, CDCl3): δ 11.84 (brs, 1H), 4.18-4.28 (m, 2H), 3.78 (s, 2H), 3.22-3.32 (m, 2H), 2.80-2.90 (m, 2H), 1.83-1.93 (m, 2H), 1.58-1.75 (m, 5H), 1.26 (t, 3H); LC-MS: [M+H]=307.1 m/z.

Workup

  1. temperaturewhile cooling the mixture
  2. customquenched with solid NaHCO3
  3. additiondiluted with 100 ml water
  4. extractionextracted with ethyl acetate (100 ml×3)
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated under vacuum
  8. customThe crude solid was triturated with diethyl ether (100 ml)

Sources & evidence

ORD record
ord-0590ca0361174b6c85a4769a4f0c7c2c
Source dataset
uspto-grants-2016_07
Patent number
US09399647B2

Reaction notes

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