Triethylamine → HCID 67252385, compound

HRID 2427281Notes

Reaction equation

HRID 2427281 reaction equation
Cl.Cl.[NH2:3][C@H:4]1[CH2:23][C:7]2[N:8]([CH2:17][C:18]3[CH:22]=[CH:21][S:20][N:19]=3)[C:9]3[CH:10]=[CH:11][C:12]([C:15]#[N:16])=[CH:13][C:14]=3[C:6]=2[CH2:5]1.C(N(CC)CC)C.N12CCN(CC1)CC2.[CH3:39][N:40]([CH3:45])[S:41](Cl)(=[O:43])=[O:42]>C(Cl)(Cl)Cl.C(Cl)Cl>[C:15]([C:12]1[CH:11]=[CH:10][C:9]2[N:8]([CH2:17][C:18]3[CH:22]=[CH:21][S:20][N:19]=3)[C:7]3[CH2:23][C@H:4]([NH:3][S:41]([N:40]([CH3:45])[CH3:39])(=[O:43])=[O:42])[CH2:5][C:6]=3[C:14]=2[CH:13]=1)#[N:16]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 9237DabcoHCID 83372Dimethylsulphamoyl chlorideHCID 67251326HCID 67251326, compound

Product 1

HCID 67252385HCID 67252385, compoundYield 75.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
54 °C

Procedure

Mix (R)-2-amino-4-isothiazol-3-ylmethyl-1,2,3,4-tetrahydro-cyclopenta[b]indole-7-carbonitrile dihydrochloride salt (1.0 g, 2.72 mmol), triethylamine (0.76 mL, 5.44 mmol), and 1,4-diazabicyclo[2,2,2]octane (0.52 g, 4.63 mmol) in CHCl3 (80 mL) and heat in an oil bath until the internal temperature reaches to 54° C. Add a solution of dimethylsulfamoyl chloride (0.35 mL, 3.26 mmol) in CHCl3 (10 mL) drop wise to the reaction mixture via addition funnel under a nitrogen atmosphere over 30 min. Stir the resulting mixture for an additional hour at 54° C. and then cool to room temperature. Dilute with CH2Cl2 (150 mL), wash the organic layer with saturated NaHCO3, dry (Na2SO4), filter, and concentrate in vacuo. Purify using silica gel chromatography on with EtOAc/hexane (8/2) to yield 0.82 g (75%) of the title compound. 1H NMR (400 MHz, DMSO-d6) δ 9.03 (s, 1H), 7.88 (s, 1H), 7.74 (d, J=5.0 Hz, 1H), 7.64 (d, J=5.1 Hz, 1H), 7.38 (d, J=5.0 Hz, 1H), 7.17 (s, 1H), 5.52 (s, 2H), 4.52-4.40 (m, 2H), 3.31-3.18 (m, 2H), 2.62 (s, 6H).

Workup

  1. temperatureheat in an oil bath until the internal temperature
  2. customreaches to 54° C
  3. additionvia addition funnel under a nitrogen atmosphere over 30 min
  4. temperaturecool to room temperature
  5. washwash the organic layer with saturated NaHCO3
  6. dry with materialdry (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate in vacuo
  9. customPurify

Sources & evidence

ORD record
ord-b971ec986b394a1d902c7642449457df
Source dataset
uspto-grants-2011_06
Patent number
US07968587B2

Reaction notes

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