Sodium Iodide → HCID 59457494, compound

HRID 1710792Notes

Reaction equation

HRID 1710792 reaction equation
ClCCCOC1C=C[C:9]([C:12]2O[CH:14]=[C:15]([CH:17]=O)[N:16]=2)=CC=1.CN1N=NC(N)=N1.C([BH3-])#N.Cl[CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[O:41][CH:42]=[C:43]([CH2:45][NH:46][C:47]3[N:48]=[N:49][N:50]([CH3:52])[N:51]=3)[N:44]=2)=[CH:36][CH:35]=1.CC1CCCN1.C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+]>O1CCCC1.C(#N)C.O.C(O)(=O)C>[CH3:52][N:50]1[N:49]=[N:48][C:47]([NH:46][CH2:45][C:43]2[N:44]=[C:40]([C:37]3[CH:38]=[CH:39][C:34]([O:33][CH2:32][CH2:31][CH2:30][N:16]4[CH2:12][CH2:9][CH2:17][CH:15]4[CH3:14])=[CH:35][CH:36]=3)[O:41][CH:42]=2)=[N:51]1

Participants

12

Reactant 7

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 130032-MethylpyrrolidineHCID 1386772-methyl-2H-1,2,3,4-tetrazol-5-amineHCID 498716Cyano-borohydrideHCID 59457459HCID 59457459, compoundHCID 59457490HCID 59457490, compound

Product 1

HCID 59457494HCID 59457494, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 2-[4-(3-chloro-propoxy)-phenyl]-oxazole-4-carbaldehyde i100 (0.042 mmol), 2-methyl-2H-tetrazol-5-ylamine (4.16 mg, 0.042 mmol, 1 eq) and cyanoborohydride supported on polystyrene (26 mg, 0.1 mmol, 2.5 eq) is suspended in tetrahydrofuran (300 μl) containing 10% acetic acid and is stirred at 65° C. overnight. The polystyrene beads are then filtered off and the resulting solution is concentrated to dryness under a stream of nitrogen and taken up in dichloromethane (2 ml). The solution is washed with 1 M potassium hydrogenosulfate (1 ml) and concentrated under reduced pressure. The residue N-({2-[4-(3-chloropropoxy)phenyl]-1,3-oxazol-4-yl}methyl)-2-methyl-2H-tetrazol-5-amine i101 is then treated with a solution of 2-methylpyrrolidine (4 mg, 1 eq) in acetonitrile (300 μl). Sodium carbonate (14 mg, 0.1 mmol, 2 eq) and sodium iodide (15 mg, 0.1 mmol, 2 eq) are added and the suspension is stirred overnight at 80° C. Water (1 ml) is then added and the mixture is extracted with dichloromethane (2×1 ml). The organic phases are concentrated and purified by preparative liquid chromatography (gradient: acetonitrile/water/hydrogen carbonate) to afford 2-methyl-N-[(2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-1,3-oxazol-4-yl)methyl]-2H-tetraazol-5-amine 139.

Workup

  1. filtrationThe polystyrene beads are then filtered off
  2. concentrationthe resulting solution is concentrated to dryness under a stream of nitrogen
  3. washThe solution is washed with 1 M potassium hydrogenosulfate (1 ml)
  4. concentrationconcentrated under reduced pressure
  5. stirringthe suspension is stirred overnight at 80° C
  6. extractionthe mixture is extracted with dichloromethane (2×1 ml)
  7. concentrationThe organic phases are concentrated
  8. custompurified by preparative liquid chromatography (gradient: acetonitrile/water/hydrogen carbonate)

Sources & evidence

ORD record
ord-43bf44dfe8da4d6f974c0358ca985d06
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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