Isopropylamine → HCID 11532852, compound

HRID 2217780Notes

Reaction equation

HRID 2217780 reaction equation
[CH3:1][CH:2]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:29])[CH:13]([NH:17][C:18](=[O:28])[CH2:19][C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=2)[CH2:14][CH2:15][CH3:16])=[N:8][N:7]=1)[CH2:3][CH:4]=O.[CH:30]([NH2:33])([CH3:32])[CH3:31].C([BH3-])#N.[Na+].S([O-])([O-])(=O)=O.[Na+].[Na+]>ClC(Cl)C.C(Cl)Cl.C(O)(=O)C>[CH:30]([NH:33][CH2:4][CH2:3][CH:2]([C:6]1[S:10][C:9]([NH:11][C:12](=[O:29])[CH:13]([NH:17][C:18](=[O:28])[CH2:19][C:20]2[CH:25]=[C:24]([F:26])[CH:23]=[C:22]([F:27])[CH:21]=2)[CH2:14][CH2:15][CH3:16])=[N:8][N:7]=1)[CH3:1])([CH3:32])[CH3:31]

Participants

8

Reactant 4

HCID 6363IsopropylamineHCID 24436Sodium SulfateHCID 5003444Sodium cyanoborohydrideHCID 11711548HCID 11711548, compound

Product 1

HCID 11532852HCID 11532852, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 2-[2-(3,5-difluoro-phenyl)-acetylamino]-pentanoic acid [5-(1-methyl-3-oxo-propyl)-[1,3,4]thiadiazol-2-yl]-amide (63 mg, 0.148 mmol), isopropylamine (0.2 ml) in dichloroethane (1 ml) and methylene chloride (1 ml) was stirred at r.t. for 10 min. Sodium cyanoborohydride (70 mg), acetic acid (0.1 ml), and sodium sulphate were added and the resulting mixture was stirred at 45-50° C. overnight. The mixture was quenched with water, basified with saturated sodium carbonate, extracted with methylene chloride. The organic layer was separated, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by Shimadzu HPLC to give the title compound LC-MS RT=1.7 min, M+1=467.9.

Workup

  1. stirringthe resulting mixture was stirred at 45-50° C. overnight
  2. customThe mixture was quenched with water
  3. extractionextracted with methylene chloride
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by Shimadzu HPLC

Sources & evidence

ORD record
ord-daf12f5fffdf4f6da2a855d51f1187f2
Source dataset
uspto-grants-2008_08
Patent number
US07408068B2

Reaction notes

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