Acetic Acid → (5-[3-Amino-5-(morpholin-4-yl)phenyl]-1,3-thiazol-2-yl)(dicyclopropyl)methanol

HRID 410534Notes

Reaction equation

HRID 410534 reaction equation
[CH:1]1([C:4]([CH:26]2[CH2:28][CH2:27]2)([C:6]2[S:7][C:8]([C:11]3[CH:16]=[C:15]([N+:17]([O-])=O)[CH:14]=[C:13]([N:20]4[CH2:25][CH2:24][O:23][CH2:22][CH2:21]4)[CH:12]=3)=[CH:9][N:10]=2)[OH:5])[CH2:3][CH2:2]1.C(O)(=O)C>C(OCC)(=O)C.[Pd]>[NH2:17][C:15]1[CH:16]=[C:11]([C:8]2[S:7][C:6]([C:4]([CH:1]3[CH2:2][CH2:3]3)([CH:26]3[CH2:28][CH2:27]3)[OH:5])=[N:10][CH:9]=2)[CH:12]=[C:13]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)[CH:14]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 67258049Dicyclopropyl{5-[3-(morpholin-4-yl)-5-nitrophenyl]-1,3-thiazol-2-yl}methanol

Product 1

HCID 67433244(5-[3-Amino-5-(morpholin-4-yl)phenyl]-1,3-thiazol-2-yl)(dicyclopropyl)methanolYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of Step 4 (239 mg, 0.595 mmol) in ethyl acetate (5.4 mL)/acetic acid (0.54 mL) was added Pd/C (10 wt %, 60 mg, 0.056 mmol) and the reaction flask was purged with N2 and then H2. The reaction was stirred for 4 hr at room temperature under H2 (balloon; 25 mg of Pd/C were added after 2 h to complete the reaction) and then filtered through a microfilter (Glass Acrodisc 25 mm) and was washed with dichloromethane. The filtrate was concentrated, stripped with toluene (3×) and then dried under vacuum overnight to provide 221 mg (0.595 mmol, quant. yield) of {5-[3-amino-5-(morpholin-4-yl)phenyl]-1,3-thiazol-2-yl}(dicyclopropyl)methanol as a fluffy solid of sufficient purity to be used directly. MS APCI: [M+H]+ m/z 372.1.

Workup

  1. customthe reaction flask was purged with N2
  2. addition25 mg of Pd/C were added after 2 h
  3. customthe reaction) and
  4. filtrationthen filtered through a microfilter (Glass Acrodisc 25 mm)
  5. washwas washed with dichloromethane
  6. concentrationThe filtrate was concentrated
  7. customdried under vacuum overnight

Sources & evidence

ORD record
ord-66b80d22839a4fafa78e9f7911fe258c
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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