HCID 57584739, compound → HCID 71584770, compound

HRID 2406332Notes

Reaction equation

HRID 2406332 reaction equation
[NH2:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][O:11][C:6]=2[C:5]([C:12]([NH:14][CH3:15])=[O:13])=[CH:4][CH:3]=1.Cl[C:17]1[N:22]=[C:21]([NH:23][CH2:24][CH3:25])[C:20]([C:26]([F:29])([F:28])[F:27])=[CH:19][N:18]=1>CC(O)(C)C>[CH2:24]([NH:23][C:21]1[C:20]([C:26]([F:28])([F:29])[F:27])=[CH:19][N:18]=[C:17]([NH:1][C:2]2[C:7]3[O:8][CH2:9][CH2:10][O:11][C:6]=3[C:5]([C:12]([NH:14][CH3:15])=[O:13])=[CH:4][CH:3]=2)[N:22]=1)[CH3:25]

Participants

4

Reactant 2

HCID 57584739HCID 57584739, compoundHCID 86687950HCID 86687950, compound

Product 1

HCID 71584770HCID 71584770, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
100 °C

Procedure

A microwave vial equipped with a magnetic stirrer was charged with 8-amino-N-methyl-2,3-dihydrobenzo[b][1,4]dioxine-5-carboxamide (50 mg, 0.18 mmol), 2-chloro-N-ethyl-5-(trifluoromethyl)pyrimidin-4-amine (40 mg, 0.18 mmol), and t-BuOH (1.0 mL). The mixture was heated at 100° C. for 2 h under microwave irradiation. It was then concentrated and the residue was purified by reverse-phase prep-HPLC to afford the title compound as white solid (15.4 mg, 32%). LCMS: ESI (10 minute run), m/z=398.1 Retention time: 5.471 minute. 1H NMR (500 MHz, CDCl3) δ 8.19 (d, J=9.0 Hz, 1H), 8.17 (s, 1H), 7.82 (d, J=4.5 Hz, 1H), 7.67˜7.62 (m, 1H), 7.50˜7.47 (m, 1H), 5.20 (s, 1H), 4.46˜4.44 (m, 2H), 4.41˜4.40 (m, 2H), 3.63˜3.56 (m, 2H), 3.01 (d, J=5.0 Hz, 3H), 1.31 (t, J=7.5 Hz, 3H).

Workup

  1. customA microwave vial equipped with a magnetic stirrer
  2. concentrationIt was then concentrated
  3. customthe residue was purified by reverse-phase prep-HPLC

Sources & evidence

ORD record
ord-41163e2bf74d444fa1ffa49da5d058fc
Source dataset
uspto-grants-2014_08
Patent number
US08809331B2

Reaction notes

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