HCID 71074957, compound → HCID 86674325, compound

HRID 1028115Notes

Reaction equation

HRID 1028115 reaction equation
[Si:1]([O:18][CH2:19][CH2:20][N:21]([CH2:42][CH2:43][O:44][Si:45]([C:58]([CH3:61])([CH3:60])[CH3:59])([C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)[C:22]1[S:23][C:24]([C:27]2[CH:32]=[C:31]([N+:33]([O-])=O)[CH:30]=[C:29]([N:36]3[CH2:41][CH2:40][O:39][CH2:38][CH2:37]3)[CH:28]=2)=[CH:25][N:26]=1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(OCC)(=O)C.C(O)(=O)C.[Pd]>[NH2:33][C:31]1[CH:32]=[C:27]([C:24]2[S:23][C:22]([N:21]([CH2:42][CH2:43][O:44][Si:45]([C:58]([CH3:61])([CH3:60])[CH3:59])([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=3)[C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[CH2:20][CH2:19][O:18][Si:1]([C:14]([CH3:17])([CH3:15])[CH3:16])([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:26][CH:25]=2)[CH:28]=[C:29]([N:36]2[CH2:41][CH2:40][O:39][CH2:38][CH2:37]2)[CH:30]=1

Participants

5

Reactant 1

HCID 71074957HCID 71074957, compound

Product 1

HCID 86674325HCID 86674325, compoundYield 99.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N,N-bis(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-5-[3-(morpholin-4-yl)-5-nitrophenyl]-1,3-thiazol-2-amine (999 mg, 1.147 mmol) in ethyl acetate (10 mL) and acetic acid (1.000 mL) at R.T., under nitrogen, was added palladium on carbon (122 mg, 0.115 mmol). The mixture was purged 3 times alternating between vacuum and H2. The reaction mixture was stirred under 1 atm H2 for 2 h. The system was evacuated with vacuum and purged 3 times alternating between vacuum and N2, and 3 mL DCM were added. The mixture was filtered through a pad of celite. The pad was rinsed with ethyl acetate and the filtrate concentrated. Residual AcOH was azeotroped with toluene (3×) to give 5-[3-amino-5-(morpholin-4-yl)phenyl]-N,N-bis(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-1,3-thiazol-2-amine as a yellow gum (958 mg, 1.139 mmol, 99%).

Workup

  1. customThe mixture was purged 3 times
  2. customThe system was evacuated with vacuum
  3. custompurged 3 times
  4. additionwere added
  5. filtrationThe mixture was filtered through a pad of celite
  6. washThe pad was rinsed with ethyl acetate
  7. concentrationthe filtrate concentrated
  8. customResidual AcOH was azeotroped with toluene (3×)

Sources & evidence

ORD record
ord-7f536f5e97da4c78b8ab5d64061236be
Source dataset
uspto-grants-2014_05
Patent number
US08735417B2

Reaction notes

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