Tert-Butylamine → HCID 57911477, compound

HRID 1099185Notes

Reaction equation

HRID 1099185 reaction equation
CC1C=CC(S(OS(C2C=CC(C)=CC=2)(=O)=O)(=O)=O)=CC=1.FC(F)(F)C1C=CC=CC=1.[F:32][C:33]1[C:38]([F:39])=[CH:37][CH:36]=[CH:35][C:34]=1[C@@H:40]1[CH2:51][CH2:50][C:49](=[O:52])[C:43]2=[N+:44]([O-])[CH:45]=[CH:46][CH:47]=[C:42]2[CH2:41]1.[CH3:53][C:54]([NH2:57])([CH3:56])[CH3:55]>C(OCC)(=O)C.C(Cl)Cl>[C:54]([NH:57][C:45]1[N:44]=[C:43]2[C:49](=[O:52])[CH2:50][CH2:51][C@@H:40]([C:34]3[CH:35]=[CH:36][CH:37]=[C:38]([F:39])[C:33]=3[F:32])[CH2:41][C:42]2=[CH:47][CH:46]=1)([CH3:56])([CH3:55])[CH3:53]

Participants

7

Reactant 4

HCID 6385Tert-ButylamineHCID 7368(Trifluoromethyl)benzeneHCID 77773Toluene-p-sulphonic anhydrideHCID 66811087HCID 66811087, compound

Product 1

HCID 57911477HCID 57911477, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

At 0° C., the 4-methylbenzenesulfonic anhydride (0.930 g, 2.85 mmol) was added to the trifluoro-toluene (3 mL)/CH2Cl2 (3.00 mL) suspension of (R)-6-(2,3-difluorophenyl)-9-oxo-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine 1-oxide (0.412 g, 1.424 mmol) and 2-methylpropan-2-amine (0.604 mL, 5.70 mmol). The reaction was stirred at 0° C. for 30 min before diluted with ethyl acetate. The crude was washed by NaOH (1N) twice and the ethyl acetate layer was separated, dried (Na2SO4), filtered and concentrated. Flash column by ethyl acetate in hexane from 0 to 40% to 60% gave the desired product (0.1861 g, 38%). MS (ESI)[M+H+]=345.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.18 (d, J=8.56 Hz, 1H) 6.95-7.10 (m, 2H) 6.82-6.95 (m, 1H) 6.60 (d, J=8.56 Hz, 1H) 4.95 (br. s., 1H) 3.45-3.58 (m, 1H) 2.91-3.05 (m, 3H) 2.73-2.85 (m, 1H) 2.13-2.27 (m, 1H) 1.95-2.11 (m, 1H) 1.43 (s, 9H).

Workup

  1. washThe crude was washed by NaOH (1N) twice
  2. customthe ethyl acetate layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-abf9b7ac79b54a999d8874d9d93a73b5
Source dataset
uspto-grants-2012_03
Patent number
US08143403B2

Reaction notes

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