Triethylamine → HCID 58551224, compound

HRID 2204276Notes

Reaction equation

HRID 2204276 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=3[O:13][C:14]3([CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:5]=2[CH:4]=[N:3]1.[CH:20]([C:22]1[CH:23]=[C:24]([CH:28]=[CH:29][C:30]=1[O:31][CH:32]([CH3:34])[CH3:33])[C:25](O)=[O:26])=[O:21].CCN=C=NCCCN(C)C.CCN(CC)CC>ClCCl>[CH:32]([O:31][C:30]1[CH:29]=[CH:28][C:24]([C:25]([N:17]2[CH2:18][CH2:19][C:14]3([C:5]4[CH:4]=[N:3][N:2]([CH3:1])[C:6]=4[C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][C:12]=4[O:13]3)[CH2:15][CH2:16]2)=[O:26])=[CH:23][C:22]=1[CH:20]=[O:21])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 585507381-Methylspiro[chromeno[4,3-c]pyrazole-4,4'-piperidine]HCID 585514031289061-37-5

Product 1

HCID 58551224HCID 58551224, compoundYield 34.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine] (250 mg, 0.76 mmol), 3-formyl-4-isopropoxy-benzoic acid (160 mg, 0.76 mmol), EDCI (160 mg, 0.84 mmol), and Et3N (430 μL, 3.1 mmol) were combined in dichloromethane (7.1 mL) and the reaction mixture was stirred at room temperature for 48 hours. The reaction mixture was washed with a 1 M HCl (×2), a saturated aqueous solution of NaHCO3 (×2) and a saturated aqueous solution of NaCl. The organic layer was dried over Na2SO4, filtered and the solvent was evaporated under reduced pressure. The crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in dichloromethane) to yield 2-isopropoxy-5-(1-methylspiro[chromeno[4,3-c]pyrazole-4,4′-piperidine]-1′-carbonyl)benzaldehyde (117 mg, 34%) as a light yellow solid. ESI-MS m/z calc. 445.2, found 446.3 (M+1)+; Retention time: 1.74 minutes (3 min run).

Workup

  1. washThe reaction mixture was washed with a 1 M HCl (×2)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was evaporated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel (0-30% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-a8da5b8b21e44f9b89aab4f789902dfe
Source dataset
uspto-grants-2016_06
Patent number
US09365588B2

Reaction notes

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