Hydrochloric Acid → HCID 86691258, compound

HRID 2409255Notes

Reaction equation

HRID 2409255 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.ClCC[CH:14]([C:18]([O-:20])=O)[C:15]([O-:17])=O.[CH:21]1([CH2:28][NH2:29])[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.[BH4-].[Na+].Cl.[CH3:33][OH:34]>O>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4]([C:33]([NH:29][CH2:28][CH:21]1[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)=[O:34])=[CH:5][N:6]2[CH:14]([CH2:15][OH:17])[CH2:18][OH:20]

Participants

8

Reactant 6

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 78194CycloheptylmethylamineHCID 913454-ChloroindoleHCID 4311764Sodium borohydrideHCID 86691259HCID 86691259, compound

Product 1

HCID 86691258HCID 86691258, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Synthesised similar to the procedure disclosed in Example 1 where X is 4-chloro indole, Y is 2-chloroethylmalonate, and Z is cycloheptylmethyl amine. The resulting product XYZ is stirred for 30 minutes at −10° C. in methanol and NaBH4 and then slowly warmed to room temperature and stirred for 2 hour. The reaction mixture is then treated with a 1N aqueous HCl solution (pH ˜8) and concentrated to obtain a residue that is taken up in water and acidified with 1N aqueous HCl solution (pH ˜6.5 to 7). The formed precipitate is then collected by filtration, washed with water, pet ether, ethyl acetate and finally with n-Pentane, then dried under vacuum. Formula: C20H27ClN2O3; Molecular Weight: 378.89; Mass/charge ratio: 378.17 (100.0%), 380.17 (32.1%), 379.17 (22.4%), 381.17 (7.3%), 380.18 (2.9%); Elemental analysis: C, 63.40; H, 7.18; Cl, 9.36; N, 7.39; O, 12.67.

Workup

  1. customSynthesised similar to the procedure
  2. concentrationconcentrated
  3. customto obtain a residue that
  4. filtrationThe formed precipitate is then collected by filtration
  5. washwashed with water, pet ether, ethyl acetate and finally with n-Pentane
  6. customdried under vacuum
  7. additionMass/charge ratio

Sources & evidence

ORD record
ord-b2368cd8fd604de687282fec77e6773c
Source dataset
uspto-grants-2014_08
Patent number
US08815892B2

Reaction notes

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