Triethylamine → HCID 11520022, compound

HRID 1867630Notes

Reaction equation

HRID 1867630 reaction equation
[NH2:1][CH:2]1[N:8]=[C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]([CH2:19][C:20]([F:23])([F:22])[F:21])[C:3]1=[O:24].C(N(CC)CC)C.FC(F)(F)[C:34](O)=[O:35].[C:39]1([CH:45]2[CH2:49][N:48]([CH:50]3[CH2:55][CH2:54][NH:53][CH2:52][CH2:51]3)[C:47](=[O:56])[NH:46]2)[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O1CCCC1.CS(C)=O>[O:24]=[C:3]1[C@H:2]([NH:1][C:34]([N:53]2[CH2:52][CH2:51][CH:50]([N:48]3[CH2:49][CH:45]([C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[NH:46][C:47]3=[O:56])[CH2:55][CH2:54]2)=[O:35])[N:8]=[C:7]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:6]2[CH:15]=[CH:16][CH:17]=[CH:18][C:5]=2[N:4]1[CH2:19][C:20]([F:21])([F:23])[F:22]

Participants

6

Reactant 3

HCID 8471Triethylamine2×HCID 107353833-Amino-5-phenyl-1-(2,2,2-trifluoroethyl)-1H-benzo[e][1,4]diazepin-2(3H)-oneHCID 68568211HCID 68568211, compound

Product 1

HCID 11520022HCID 11520022, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3-Amino-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)-2,3-dihydro-1H-1,4-benzodiazepine (20.0 mg, 0.06 mmol) and p-nitrophenylchloroformate (12.1 mg, 0.06 mmol) were dissolved in tetrahydrofuran (0.5 mL) under argon, and cooled to 0° C. Triethylamine (8.4 uL, 0.06 mmol) was added and the reaction stirred for 1 h, followed by addition of more triethylamine (21 uL) and 4-phenyl-1-piperidin-4-ylimidazolidin-2-one trifluoroacetic acid salt (21.6 mg, 0.06 mmol), in dimethylsulfoxide (0.5 mL). The reaction was warmed to room temperature and stirred overnight. The crude product was purified by reverse phase HPLC (C-18, 5% to 95% 0.1% trifluoroacetic acid/acetonitrile in 0.1% aqueous trifluoroacetic acid gradient elution) to give the title compound (18.5 mg). MS 605.2459 (M+1)

Workup

  1. temperatureThe reaction was warmed to room temperature
  2. stirringstirred overnight
  3. customThe crude product was purified by reverse phase HPLC (C-18, 5% to 95% 0.1% trifluoroacetic acid/acetonitrile in 0.1% aqueous trifluoroacetic acid gradient elution)

Sources & evidence

ORD record
ord-193c8c23a0ba4e1ba2ba7dabf1231926
Source dataset
uspto-grants-2009_12
Patent number
US07632832B2

Reaction notes

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