Ethyl chloroformate → HCID 10274903, compound

HRID 2416637Notes

Reaction equation

HRID 2416637 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]3[CH:13]=[CH:14][C:15]([C:17]4[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[N:18]=4)=[CH:16][C:9]=23)[CH:5]=[CH:6][CH:7]=1.Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26].C(N(C(C)C)CC)(C)C>O1CCOCC1.CS(C)=O>[CH2:28]([O:27][C:25](=[O:26])[NH:23][C:19]1[N:18]=[C:17]([C:15]2[CH:14]=[CH:13][C:10]3=[N:11][O:12][C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Br:1])[CH:3]=4)=[C:9]3[CH:16]=2)[CH:22]=[CH:21][N:20]=1)[CH3:29]

Participants

6

Reactant 3

HCID 10928Ethyl chloroformateHCID 81531DiisopropylethylamineHCID 22632292HCID 22632292, compound

Product 1

HCID 10274903HCID 10274903, compoundYield 33.3%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

To a stirring solution of 4-[3-(3-bromophenyl)-benzo[c]isoxazol-5-yl]-pyrimidin-2-ylamine (75 mg; 0.205 mmol) in 1 mL of p-dioxane and 0.5 mL of DMSO, was added 40 μL (45.6 mg, 0.42 mmol) of ethyl chloroformate followed by 73 μL (54.3 mg, 0.42 mmol) of diisopropylethylamine. The reaction was stirred at 50° C., in a sealed vessel, for 8 hours. The solvents were removed under vacuo and the crude material was purified via HPLC with acetonitrile/water/TFA as the eluent. The material was isolated as a yellow powder (30 mg, 32% yield). 1H NMR (500 MHz, DMSO-d6) δ 10.5 (br s,1H), 8.9 (s, 1H), 8.75 (d, 1H), 8.35 (m, 3H), 8.3(s, 1H), 8.0 (d, 1H), 7.89 (t, 2H), 7.65 (t, 1H), 4.2 (q, 2H), 1.26 (t, 3H) in ppm. LC-MS (ES+) m/e=439/441 (M+H)

Workup

  1. customThe solvents were removed under vacuo
  2. customthe crude material was purified via HPLC with acetonitrile/water/TFA as the eluent

Sources & evidence

ORD record
ord-bf1c7b8f6a7b4a06b355f3127332f59d
Source dataset
uspto-grants-2004_11
Patent number
US06825190B2

Reaction notes

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