HCID 59761158, compound → HCID 178480363, compound

HRID 600512Notes

Reaction equation

[N:1]1([C:5]([C:7]2[CH:42]=[CH:41][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:30]=[C:31]([O:33][C@H:34]4[CH2:38][CH2:37][N:36]([CH3:39])[C:35]4=[O:40])[CH:32]=3)[C:15]([NH:17][C:18]3[CH:22]=[CH:21][N:20](C(OC(C)(C)C)=O)[N:19]=3)=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1>C(#N)C>[N:1]1([C:5]([C:7]2[CH:42]=[CH:41][C:10]([O:11][C:12]3[CH:13]=[C:14]([CH:30]=[C:31]([O:33][C@H:34]4[CH2:38][CH2:37][N:36]([CH3:39])[C:35]4=[O:40])[CH:32]=3)[C:15]([NH:17][C:18]3[CH:22]=[CH:21][NH:20][N:19]=3)=[O:16])=[CH:9][CH:8]=2)=[O:6])[CH2:4][CH2:3][CH2:2]1

Participants

Conditions

Temperature: 150 °C

Procedure

Tert-butyl 3-[[3-[4-(azetidine-1-carbonyl)phenoxy]-5-[(3S)-1-methyl-2-oxo-pyrrolidin-3-yl]oxy-benzoyl]amino]pyrazole-1-carboxylate (Intermediate 14) (388 mg, 0.67 mmol) was dissolved in acetonitrile (5 mL) and heated in a microwave for 12 minutes at 150° C., the solution was concentrated under reduced pressure to afford the product (261 mg, 82%). 1H NMR δ (300 MHz, CDCl3) 2.06-2.21 (m, 1H), 2.34 (quintet, 2H), 2.49-2.63 (m, 1H), 2.92 (s, 3H), 3.31-3.52 (m, 2H), 4.15-4.38 (m, 4H), 4.87 (t, 1H), 6.77 (s, 1H), 6.80 (s, 1H), 6.98 (d, 2H), 7.17 (s, 1H), 7.38 (s, 1H), 7.48 (s, 1H), 7.61 (d, 2H), 10.29 (s, 1H); m/z 476 (M+H)+.

Workup

concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record: ord-ebff90263a0846ea90a378df9cf80983
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902200B2

Reaction notes

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