Dabco → HCID 11547946, compound

HRID 2117067Notes

Reaction equation

HRID 2117067 reaction equation
Cl[C:2]1[C:7]2=[C:8]([CH3:16])[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][N:6]2[N:5]=[CH:4][N:3]=1.C1N2CCN(CC2)C1.[F:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33]([NH:35][C:36]([NH:38][C:39]2[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=2)=[S:37])=[O:34])=[CH:28][CH:27]=1>C(#N)C>[F:25][C:26]1[CH:27]=[CH:28][C:29]([CH2:32][C:33]([NH:35][C:36](=[S:37])[NH:38][C:39]2[CH:44]=[CH:43][C:42]([O:45][C:2]3[C:7]4=[C:8]([CH3:16])[C:9]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:10][N:6]4[N:5]=[CH:4][N:3]=3)=[CH:41][CH:40]=2)=[O:34])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 9237DabcoHCID 17998719Ethyl 4-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylateHCID 21081466HCID 21081466, compound

Product 1

HCID 11547946HCID 11547946, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a room temperature solution of ethyl 4-chloro-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (7.2 mg, 0.03 mmol) (for preparation see U.S. Pat. No. 6,670,357, the disclosure of which is herein incorporated by reference) and DABCO (7 mg, 0.06 mmol) in acetonitrile (0.5 mL) was added 1-(2-(4-fluorophenyl)acetyl)-3-(4-hydroxyphenyl)thiourea (0.5 mL, 0.05 mmol). The reaction was shaken at room temperature. After 30 min, LC/MS analysis indicated mostly product. The reaction was stirred at room temperature overnight. The mixture was evaporated to dryness. Purification by silica gel chromatography (eluting with 1% methanol/dichloromethane) provided the desired product contaminated with impurities. A second purification by silica gel chromatography (1-6% Ethyl acetate/dichloromethane) again did not remove all of the impurities. The resulting solid mixture was washed with methanol and dried to provide the title compound (6 mg, 39%) as a yellow solid. 1H NMR (CDCl3) δ 12.32 (s, 1H), 8.62 (s, 1H), 8.16 (s, 1H), 7.91 (s, 1H), 7.76 (m, 2H), 7.29 (m, 4H), 7.12 (m, 2H), 4.38 (q, 2H, J=7.1 Hz), 3.72 (s, 2H), 2.82 (s, 3H), 1.40 (t, 3H, J=7.1 Hz); MS(ESI+) m/z 508 (M+H)+.

Workup

  1. stirringThe reaction was stirred at room temperature overnight
  2. customThe mixture was evaporated to dryness
  3. customPurification
  4. washby silica gel chromatography (eluting with 1% methanol/dichloromethane)

Sources & evidence

ORD record
ord-b658c76cf5994237bb2255a01e658885
Source dataset
uspto-grants-2008_10
Patent number
US07439246B2

Reaction notes

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