HCID 57991969, compound → HCID 86636673, compound

HRID 2075335Notes

Reaction equation

HRID 2075335 reaction equation
[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][C:9]([C:11]3[S:15][C:14]([NH:16][C:17](=O)[C@@H:18]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)=[N:13][N:12]=3)=[CH:10][C:3]=12.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1>C1COCC1>[Cl:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][C:9]([C:11]3[S:15][C:14]([NH:16][CH2:17][C@@H:18]([NH:30][C:31](=[O:37])[O:32][C:33]([CH3:35])([CH3:34])[CH3:36])[CH2:19][C:20]4[CH:25]=[CH:24][CH:23]=[C:22]([C:26]([F:29])([F:28])[F:27])[CH:21]=4)=[N:13][N:12]=3)=[CH:10][C:3]=12

Participants

4

Reactant 2

HCID 57991969HCID 57991969, compoundHCID 68718528lithium aluminium hydride THF

Product 1

HCID 86636673HCID 86636673, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

tert-Butyl (S)-1-(5-(4-chlorothieno[2,3-c]pyridin-2-yl)-1,3,4-thiadiazol-2-ylamino)-1-oxo-3-(3-(trifluoromethyl)phenyl)propan-2-ylcarbamate was dissolved in 10 mL THF and cooled to 0° C. in a round bottom flask under nitrogen. To this flask was added 5 mL of a 1 N LiAlH4 THF solution dropwise. The resulting mixture was stirred from 0° C. to 20° C. in 2 hours and then at 20° C. for 3 hours. The reaction mixture was diluted with 20 mL THF and quenched with addition of 2 grams of Na2SO4.10H2O. After the mixture was stirred for 16 hours, it was filtered through a pad of celite. THF was removed under reduced pressure, and the remaining residue was subjected to a silica gel flash column chromatograph separation using 40% EtOAc in hexane as the eluant to yield the desired product (0.075 g, two steps y=13%) as a white solid. LCMS (API-ES) m/z (%): 570.2 (100%, M++H).

Workup

  1. waitat 20° C. for 3 hours
  2. customquenched with addition of 2 grams of Na2SO4.10H2O
  3. stirringAfter the mixture was stirred for 16 hours
  4. filtrationit was filtered through a pad of celite
  5. customTHF was removed under reduced pressure
  6. customthe remaining residue was subjected to a silica gel flash column chromatograph separation

Sources & evidence

ORD record
ord-d165edecdb904d64ba0b13322f3db8cd
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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