Triethylamine → HCID 178426904, compound

HRID 1908174Notes

Reaction equation

HRID 1908174 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:15]3[N:16]=[CH:17][NH:18][C:14]=3[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[O:7]2)[CH2:3][CH2:2]1.[CH:19]([O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][C:24]=1[CH3:32])([CH3:21])[CH3:20].C(N(CC)CC)C.CCN=C=NCCCN(C)C>ClCCl>[CH:19]([O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([N:1]2[CH2:6][CH2:5][C:4]3([C:15]4[N:16]=[CH:17][NH:18][C:14]=4[C:13]4[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=4[O:7]3)[CH2:3][CH2:2]2)=[O:28])=[CH:25][C:24]=1[CH3:32])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 592729354-Isopropoxy-3-methylbenzoic acidHCID 178419910HCID 178419910, compound

Product 1

HCID 178426904HCID 178426904, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 1H-spiro[chromeno[3,4-d]imidazole-4,4′-piperidine] (210 mg, 0.88 mmol), 4-isopropoxy-3-methyl-benzoic acid (170 mg, 0.89 mmol), triethylamine (370 μL, 2.6 mmol), and EDCI (170 mg, 0.89 mmol) in dichloromethane (5 mL) was stirred for 16 h. The reaction mixture was diluted with dichloromethane and was washed with 1M HCl, saturated solution of NaHCO3, and brine. The organics were dried over sodium sulfate and evaporated to dryness. The crude product was purified by silica gel chromatography eluting with 0-100% methanol in dichloromethane to yield (4-isopropoxy-3-methylphenyl)(1H-spiro[chromeno[3,4-d]imidazole-4,4′-piperidine]-1′-yl)methanone (44 mg, 12%). ESI-MS m/z calc. 417.5. found 418.5 (M+1)+; Retention time: 1.44 minutes (3 min run).

Workup

  1. washwas washed with 1M HCl, saturated solution of NaHCO3, and brine
  2. dry with materialThe organics were dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe crude product was purified by silica gel chromatography
  5. washeluting with 0-100% methanol in dichloromethane

Sources & evidence

ORD record
ord-f464200e49254054a3785f0823f06411
Source dataset
uspto-grants-2013_12
Patent number
US08598164B2

Reaction notes

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