HCID 73063680, compound → 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(2-hydroxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide

HRID 1767028Notes

Reaction equation

HRID 1767028 reaction equation
C([O:8][CH2:9][C:10]([C:13]1[S:17][C:16]([NH:18][C:19](=[O:37])[CH:20]([NH:24][CH:25]2[CH2:34][CH2:33][C:32]3[C:27](=[C:28]([F:36])[CH:29]=[C:30]([F:35])[CH:31]=3)[CH2:26]2)[CH2:21][CH2:22][CH3:23])=[N:15][N:14]=1)([CH3:12])[CH3:11])C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[OH:8][CH2:9][C:10]([C:13]1[S:17][C:16]([NH:18][C:19](=[O:37])[CH:20]([NH:24][CH:25]2[CH2:34][CH2:33][C:32]3[C:27](=[C:28]([F:36])[CH:29]=[C:30]([F:35])[CH:31]=3)[CH2:26]2)[CH2:21][CH2:22][CH3:23])=[N:15][N:14]=1)([CH3:11])[CH3:12]

Participants

4

Reactant 1

HCID 73063680HCID 73063680, compound

Product 1

HCID 729839612-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(2-hydroxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(6,8-difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(2-benzyloxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide (300 mg) in ethyl acetate (20 mL) was treated with 600 mg of 10% Pd/C (50% water) and hydrogenated at 45 psi overnight. The mixture was filtered through celite, washed with ethylacetate. The combined filtrate was concentrated to dryness, added ethanol (10 mL), ethyl acetate (10 mL) and chloroform (5 mL) and treated with 1.4 g of 10% Pd/C (50% water) and hydrogenated at 50 psi overnight. The mixture was filtered through celite, washed with a mixture of methanol and chloroform. The filtrate was concentrated to give a light yellow oil. The oil was triturated with a 5:1 of hexane:chloroform to give 2-(6,8-Difluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid [5-(2-hydroxy-1,1-dimethyl-ethyl)-[1,3,4]thiadiazol-2-yl]-amide as an off-white solid, LC-MS RT=1.8 min, M+1=439.0.

Workup

  1. filtrationThe mixture was filtered through celite
  2. washwashed with ethylacetate
  3. concentrationThe combined filtrate was concentrated to dryness
  4. additionadded ethanol (10 mL), ethyl acetate (10 mL) and chloroform (5 mL)
  5. additiontreated with 1.4 g of 10% Pd/C (50% water) and hydrogenated at 50 psi overnight
  6. filtrationThe mixture was filtered through celite
  7. washwashed with a mixture of methanol and chloroform
  8. concentrationThe filtrate was concentrated
  9. customto give a light yellow oil
  10. customThe oil was triturated with a 5:1 of hexane

Sources & evidence

ORD record
ord-680f0f82a64642f68e2e9f8b3a13c322
Source dataset
uspto-grants-2007_06
Patent number
US07232820B2

Reaction notes

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