Triphenylphosphine → HCID 67298266, compound

HRID 1520397Notes

Reaction equation

[OH:1][CH2:2][C:3]1[CH:13]=[CH:12][C:6]2[N:7]([CH3:11])[C:8](=[O:10])[O:9][C:5]=2[CH:4]=1.[CH3:14][NH:15][C:16]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([C:26]3[CH:27]=[C:28](O)[CH:29]=[CH:30][CH:31]=3)[CH:24]=2)[N:19]=[C:18]([C:33]2[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=2)[N:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>C1COCC1>[CH3:11][N:7]1[C:6]2[CH:12]=[CH:13][C:3]([CH2:2][O:1][C:30]3[CH:29]=[CH:28][CH:27]=[C:26]([C:23]4[CH:24]=[C:25]5[C:20](=[CH:21][CH:22]=4)[N:19]=[C:18]([C:33]4[CH:34]=[N:35][CH:36]=[CH:37][CH:38]=4)[N:17]=[C:16]5[NH:15][CH3:14])[CH:31]=3)=[CH:4][C:5]=2[O:9][C:8]1=[O:10]

Participants

Conditions

Temperature: 50 °C

Procedure

To 6-(hydroxymethyl)-3-methylbenzo[d]oxazol-2(3H)-one (45.1 μmol) was added the solution of 3-(4-(methylamino)-2-(pyridin-3-yl)quinazolin-6-yl)phenol (30 μmol) in THF (400 μL). After PS-triphenylphosphine (60 μmol) was added, the solution of DBAD (di-tert-butyl azodicarboxylate, 66 mmol) in THF was dispensed to the vials. The mixture was heated at 50° C. for 8 h. After the solvent was removed, the residue was diluted with methanol and purified by Mass triggered PREP-HPLC Condition D. The target fraction was lyophilized to afford the titled compound whose structure was finally confirmed by LCMS using LCMS Method E.

Workup

customAfter the solvent was removed
additionthe residue was diluted with methanol
custompurified by Mass

Sources & evidence

ORD record: ord-17fb77be2ebd484e878d4d688d24980e
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073890B2

Reaction notes

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