Potassium Carbonate → HCID 66716937, compound

HRID 1184509Notes

Reaction equation

[CH3:1][CH:2]1[O:7][C:6]2[CH:8]=[CH:9][C:10]([O:12][CH:13]3[CH2:18][CH2:17][NH:16][CH2:15][CH2:14]3)=[CH:11][C:5]=2[NH:4][C:3]1=[O:19].C([O-])([O-])=O.[K+].[K+].F[C:27]1[CH:36]=[CH:35][C:30]([C:31]([NH:33][CH3:34])=[O:32])=[CH:29][CH:28]=1>CS(C)=O>[CH3:34][NH:33][C:31](=[O:32])[C:30]1[CH:35]=[CH:36][C:27]([N:16]2[CH2:17][CH2:18][CH:13]([O:12][C:10]3[CH:9]=[CH:8][C:6]4[O:7][CH:2]([CH3:1])[C:3](=[O:19])[NH:4][C:5]=4[CH:11]=3)[CH2:14][CH2:15]2)=[CH:28][CH:29]=1

Participants

Conditions

Temperature: 120 °C

Procedure

In a 4 mL screw cap vial, 2-methyl-6-(piperidin-4-yloxy)-2H-benzo[b][1,4]oxazin-3(4H)-one 394E (0.054 g, 0.206 mmol), K2CO3 (0.142 g, 1.029 mmol), and 4-fluoro-N-methylbenzamide (0.038 g, 0.247 mmol) were suspended in DMSO (0.412 mL) to give a brown suspension. The reaction was stirred at 120° C. for 72 hr. The crude material was purified by prep HPLC-MS (40-75% MeCN in water). The fractions were collected and concentrated in vacuo affording the product as a tan solid (0.0186 g, 22.85% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34-1.47 (m, 3H) 1.59-1.74 (m, 2H) 1.93-2.07 (m, 2H) 2.71-2.82 (m, 3H) 3.09-3.23 (m, 2H) 3.61 (br. s., 2H) 4.38-4.50 (m, 1H) 4.58 (q, J=6.65 Hz, 1H) 4.68 (d, J=6.57 Hz, 1H) 6.50 (d, J=2.78 Hz, 1H) 6.53-6.62 (m, 1H) 6.67 (dd, J=8.72, 2.91 Hz, 1H) 6.88 (d, J=8.84 Hz, 1H) 6.94-7.06 (m, 2H) 7.71 (d, J=8.84 Hz, 2H) 7.81-7.88 (m, 1H) 8.10-8.20 (m, 1H) 10.57 (s, 1H). ESI-MS: m/z 396.3 (M+H)+.

Workup

customIn a 4 mL screw cap vial
customto give a brown suspension
customThe crude material was purified by prep HPLC-MS (40-75% MeCN in water)
customThe fractions were collected
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-21b8cd18986846d6847bb82b64fac6cd
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669249B2

Reaction notes

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