1-Heptanamine → HCID 67617631, compound

HRID 1029740Notes

Reaction equation

HRID 1029740 reaction equation
[F:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][NH:11][N:12]1[C:20]2[C:15](=[CH:16][C:17]([OH:21])=[CH:18][CH:19]=2)[C:14]([CH3:22])=[CH:13]1.[C:23](C1NC=CN=1)(C1NC=CN=1)=[O:24].[CH2:35]([NH2:42])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].C([O-])(O)=O.[Na+]>O1CCCC1.C(O)(=O)C.CCOCC>[CH2:35]([NH:42][C:23](=[O:24])[O:21][C:17]1[CH:16]=[C:15]2[C:20](=[CH:19][CH:18]=1)[N:12]([NH:11][CH2:10][CH2:9][CH2:8][C:7]1[CH:6]=[CH:5][N:4]=[CH:3][C:2]=1[F:1])[CH:13]=[C:14]2[CH3:22])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

Participants

8

Reactant 4

HCID 81271-Heptanamine2×HCID 516892Sodium BicarbonateHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 70146441HCID 70146441, compound

Product 1

HCID 67617631HCID 67617631, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent3×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution consisting of 1-[(3-fluoro-4-pyridinyl)propylamino]-3-methyl-1H-indol-5-ol (2.54 g) and anhydrous tetrahydrofuran (57 ml) was added carbonyl diimidazole (2.75 g) under nitrogen with stirring. The resulting reaction mixture was stirred at room temperature for two days, at which time acetic acid (1.65 ml) was added followed by a solution of heptylamine (1.89 ml) in tetrahydrofuran (5 ml) and acetic acid (0.76 ml). After stirring for 24 hours, an additional equivalent of heptylamine (1.26 ml) in tetrahydrofuran (5 ml) and acetic acid (0.52 ml) was added. After an additional 24 hours the reaction was complete and the reaction mixture was poured into NaHCO3 (aq.) and ether. The layers were separated and the aqueous phase was extracted with ether (3x). The combined organic layers were washed successively with NaHCO3 (aq.) and brine. Drying (Na2SO4), filtration and concentration gave a crude product. Purification via flash column chromatography (silica gel, 30% EtOAc/hexane) afforded 3.38 g of the desired product as an oil. Addition of ether and pentane solidified the product. The solid was filtered and washed with pentane, m.p. 90°-93° C.

Workup

  1. customThe resulting reaction mixture
  2. additionwas added
  3. stirringAfter stirring for 24 hours
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with ether (3x)
  6. washThe combined organic layers were washed successively with NaHCO3 (aq.) and brine
  7. customDrying
  8. filtration(Na2SO4), filtration and concentration
  9. customgave a crude product
  10. customPurification via flash column chromatography (silica gel, 30% EtOAc/hexane)

Sources & evidence

ORD record
ord-f7052df39bb14c12ac1b2c6489276d1e
Source dataset
uspto-grants-1992_04
Patent number
US05102891

Reaction notes

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