1,2,3,4-Tetrahydroquinoline → HCID 86623713, compound

HRID 901966Notes

Reaction equation

HRID 901966 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30](=[O:42])[NH:31][CH:32]([C:34]1[S:35][CH:36]=[C:37]([C:39]([OH:41])=O)[N:38]=1)[CH3:33])([CH3:28])([CH3:27])[CH3:26].C(N(C(C)C)CC)(C)C.[NH:52]1[C:61]2[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=2)[CH2:55][CH2:54][CH2:53]1>CN(C=O)C>[C:25]([O:29][C:30](=[O:42])[NH:31][CH:32]([C:34]1[S:35][CH:36]=[C:37]([C:39]([N:52]2[C:61]3[C:56](=[CH:57][CH:58]=[CH:59][CH:60]=3)[CH2:55][CH2:54][CH2:53]2)=[O:41])[N:38]=1)[CH3:33])([CH3:26])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 694601,2,3,4-TetrahydroquinolineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 21634039605667-95-6

Product 1

HCID 86623713HCID 86623713, compoundYield 63.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HBTU (306 mg, 0.81 mmol) was added to a solution of tert-butyl(1-(4-carboxythiazol-2-yl)ethyl)carbamate (200 mg, 0.73 mmol) in DMF (5 ml) at room temperature. Diisopropylethylamine (0.26 ml, 190 mg, 1.5 mmol) and 1,2,3,4-tetrahydroquinoline (0.11 ml, 117 mg, 0.88 mmol) were added and the mixture was stirred for 18 h. The mixture was partitioned between ethyl acetate and 1N hydrochloric acid and separated. The organic layer was washed with water and brine, dried and reduced. Chromatography (45% EtOAc/55% hexanes) afforded tert-butyl(1-(4-(1,2,3,4-tetrahydroquinoline-1-carbonyl) thiazol-2-yl)ethyl)carbamate (180 mg, 63%).

Workup

  1. customThe mixture was partitioned between ethyl acetate and 1N hydrochloric acid
  2. customseparated
  3. washThe organic layer was washed with water and brine
  4. customdried

Sources & evidence

ORD record
ord-b040ea657353429199a343e3c38dcc68
Source dataset
uspto-grants-2008_04
Patent number
US07365065B2

Reaction notes

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