4-Methylmorpholine → HCID 178452470, compound

HRID 1520760Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[C:21]1([C:27]2[CH:31]=[C:30]([C:32](O)=[O:33])[NH:29][N:28]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN1CCOCC1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>O.CN(C=O)C>[C:21]1([C:27]2[NH:28][N:29]=[C:30]([C:32]([NH:1][C:2]3[CH:7]=[CH:6][C:5]([C@@H:8]4[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]4)=[CH:4][CH:3]=3)=[O:33])[CH:31]=2)[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 60 °C

Procedure

In a 25 mL round-bottomed flask, (S)-tert-butyl 2-(4-aminophenyl)morpholine-4-carboxylate (100 mg, 359 μmol, Eq: 1.00), 3-phenyl-1H-pyrazole-5-carboxylic acid (87.9 mg, 467 μmol, Eq: 1.3) (CAS-1134-49-2), N-Methylmorpholine (109 mg, 118 μl, 1.08 mmol, Eq: 3) and HBTU (204 mg, 539 μmol, Eq: 1.5) were combined with DMF (3.75 ml). The reaction mixture was stirred at 60° C. for 16.5 hours. The mixture was poured into water (10 ml) and extracted twice with EtOAc. The organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude material was purified by column chromatography. (6 g silica gel (63-200A), eluent: heptane/EtOAc 2:1) to give the title compound as a white solid (120 mg, 74.5%). MS (ISP): 449.5 ([M+H]+).

Workup

extractionextracted twice with EtOAc
washThe organic layers were washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe crude material was purified by column chromatography

Sources & evidence

ORD record: ord-919672a21cf345c6936d7ad14722f433
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073911B2

Reaction notes

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