Diisopropylethylamine → HCID 16041239, compound

HRID 418687Notes

Reaction equation

HRID 418687 reaction equation
Cl[C:2](Cl)([O:4]C(=O)OC(Cl)(Cl)Cl)Cl.[F:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]2[CH2:24][CH2:23][NH:22][C:21]2=[O:25])=[CH:16][CH:15]=1.[NH2:26][C:27]1[CH:51]=[CH:50][C:30]([O:31][C:32]2[CH:37]=[CH:36][N:35]=[C:34]3[CH:38]=[C:39]([C:41]4[CH2:46][CH2:45][N:44]([C:47](=O)C)[CH2:43][CH:42]=4)[S:40][C:33]=23)=[C:29]([F:52])[CH:28]=1.CCN(C(C)C)C(C)C>C1COCC1.CO>[F:52][C:29]1[CH:28]=[C:27]([NH:26][C:2]([N:22]2[CH2:23][CH2:24][N:20]([C:17]3[CH:16]=[CH:15][C:14]([F:13])=[CH:19][CH:18]=3)[C:21]2=[O:25])=[O:4])[CH:51]=[CH:50][C:30]=1[O:31][C:32]1[CH:37]=[CH:36][N:35]=[C:34]2[CH:38]=[C:39]([C:41]3[CH2:46][CH2:45][N:44]([CH3:47])[CH2:43][CH:42]=3)[S:40][C:33]=12

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 94429TriphosgeneHCID 14807851-(4-Fluorophenyl)imidazolidin-2-oneHCID 59457670HCID 59457670, compound

Product 1

HCID 16041239HCID 16041239, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triphosgene (209.2, 0.47 mmol) was added to a solution of 1-(4-fluorophenyl)imidazolidin-2-one (209.2 mg, 0.71 mmol) in THF (4.7 mL) and the mixture was heated to reflux for 6 h. 1-(4-(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)-5,6-dihydropyridin-1(2H)-yl)ethanone 270 (120.0 mg, 0.31 mmol) and DIPEA (0.1 mL, 0.5 mmol) were added and the mixture was stirred for 1 h at room temperature. The reaction mixture was transferred to a silica gel flash chromatography column and eluted with 3% MeOH in DCM affording 264 (97.6 mg, 0.16 mmol, 52% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 10.55 (s, 1H), 8.47 (d, 5.5 Hz, 1H), 7.84 (dd, J=2.4 Hz, 13.1 Hz, 1H), 7.71-7.63 (m, 2H), 7.54 (m, 1H), 7.48-7.42 (m, 2H), 7.31-7.27 (m, 2H), 6.63 (m, 1H), 6.42 (m, 1H), 4.21 (br, 1H), 4.15 (br, 1H), 3.96-3.93 (m, 4H), 3.71-3.65 (m, 2H), 2.70 (br, 1H), 2.59 (br, 1H), 2.09 (s, 1.5H), 2.05 (s, 1.5H). MS (m/z): (M+1) 590.2 (100%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 h

Sources & evidence

ORD record
ord-f93de61a47c24fb5a3c42b943033670e
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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