Triethylamine → HCID 15292769, compound

HRID 2210608Notes

Reaction equation

HRID 2210608 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([C:26]6[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=6)=[CH:23][CH:24]=5)[N:19]([CH2:33][CH2:34][NH2:35])[CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1.C(N(CC)CC)C.[CH3:43][S:44](Cl)(=[O:46])=[O:45]>C1COCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([C:26]6[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=6)=[CH:23][CH:24]=5)[N:19]([CH2:33][CH2:34][NH:35][S:44]([CH3:43])(=[O:46])=[O:45])[CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15292764HCID 15292764, compound

Product 1

HCID 15292769HCID 15292769, compoundYield 189.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(pyridin-3-yl)-7-[1-(2-aminoethyl)-6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H-pyrrolo[1,2-c]thiazole (0.20 g, 0.062 mmol), prepared according to the method of Example 59, and triethylamine (13 μL, 0.093 mmol) in THF (15 mL) was added methanesulfonyl chloride (6 μL, 0.074 mmol). The reaction mixture was stirred for two hours at ambient temperature. The reaction mixture was quenched with saturated aqueous NH4Cl and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. 3-(Pyridin-3-yl)-7-[1-(2-methanesulfonylaminoethyl)-6-(4-fluorophenyl)indol-3-ylcarbonyl]-1H,3H-pyrrolo[1,2-c]thiazole (66 mg) was obtained by flash chromatography on silica gel (98:2 CHCl3, methanol), 1H NMR (CDCl3, 300 MHz) δ2.83 (s, 3H), 3.6 (d, 2H, J=6 Hz), 4.42-4.52 (m, 3H), 4.65 (d, 1H, J=15 Hz), 5.57 (bs, 1H), 6.38 (bs, 1H), 6.46 (bs, 1H), 6.8 (d, 1H, J=3 Hz), 7.15 (t, 2H, J=9 Hz, 11 Hz), 7.47 (d, 2H, J=7 Hz), 7.52 7.65 (m, 3H), 7.8 (d, 1H, J=9 Hz), 7.95 (s, 1H), 8.38 (d, 1H, 9 Hz), 8.55 (bs, 2H). MS (DCI/NH3) m/e 561 (M+H)+. Anal calcd for C29H25FN4O3S2 : C, 62.13; H, 4.49; N, 9.99. Found: C, 61.37; H, 4.57; N, 9.58.

Workup

  1. customThe reaction mixture was quenched with saturated aqueous NH4Cl
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-148b1d30e199435f8abe9b696e43855f
Source dataset
uspto-grants-1995_10
Patent number
US05459152

Reaction notes

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