Hydrochloric Acid → HCID 67468512, compound

HRID 1908018Notes

Reaction equation

HRID 1908018 reaction equation
O[CH:2]=[C:3]1[C:12]2([CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)[O:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]1=O.[NH2:26][N:27]([CH2:35][CH2:36][O:37][CH3:38])C(=O)OC(C)(C)C.[ClH:39].O1CCOCC1>C(O)C>[ClH:39].[CH3:38][O:37][CH2:36][CH2:35][N:27]1[C:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[O:11][C:12]3([CH2:13][CH2:14][NH:15][CH2:16][CH2:17]3)[C:3]=2[CH:2]=[N:26]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 58551531tert-Butyl 1-(2-methoxyethyl)hydrazine-1-carboxylateHCID 67468545HCID 67468545, compound

Product 1

HCID 67468512HCID 67468512, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of tert-butyl 3-(hydroxymethylene)-4-oxospiro[chroman-2,4′-piperidine]-1′-carboxylate (200 mg, 0.58 mmol) and tert-butyl N-amino-N-(2-methoxyethyl)carbamate (130 mg, 0.70 mmol) in ethanol (5 mL) was allowed to stir at rt for 2 h. A solution of hydrogen chloride in 1,4-dioxane (150 μL of 4.0 M, 0.60 mmol) was added and the mixture was stirred at 50° C. for 1.5 h before it was concentrated in vacuo to give 1-(2-methoxyethyl)-1H-spiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]hydrochloride (85 mg, 44%). ESI-MS m/z calc. 299.2. found 300.3 (M+1)+; Retention time: 0.95 minutes (3 min run).

Workup

  1. stirringthe mixture was stirred at 50° C. for 1.5 h before it
  2. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-3dbbb903e0f3469e8c354dafc1ad68af
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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