Diisopropylethylamine → HCID 58015499, compound

HRID 219294Notes

Reaction equation

[F:1][C:2]1[C:3]([NH:14][NH:15][C:16](=[O:30])[C@H:17]([N:19]2[CH:28]=[CH:27][C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]2=[O:29])[CH3:18])=[N:4][CH:5]=[C:6]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[CH:9]=2)[CH:7]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.Cl.O=C1N([C@H](C)C(O)=O)C=CC2N=CC=CC1=2.FC1C(NN)=NC=C(C2ON=C(C)C=2)C=1.CCN(C(C)C)C(C)C>C(#N)C.CO>[NH4+:4].[OH-:12].[F:1][C:2]1[C:3]([NH:14][NH:15][C:16](=[O:30])[C@H:17]([N:19]2[CH:28]=[CH:27][C:26]3[N:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:20]2=[O:29])[CH3:18])=[N:4][CH:5]=[C:6]([C:8]2[O:12][N:11]=[C:10]([CH3:13])[CH:9]=2)[CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

(2R)—N′-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanehydrazide HATU (9.0 g, 24 mmol), (R)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanoic acid hydrochloride and 1-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)hydrazine (3.6 g, 17 mmol) were taken up in acetonitrile (52 ml, 0.3 M) and cooled to 0° C. DIPEA (8.2 ml, 47 mmol) was added dropwise and the reaction was allowed to stir to room temperature for 30 minutes until complete by LCMS. The crude material was concentrated onto silica gel and then purified via MPLC eluting with 100% DCM to 90% DCM:10% MeOH:1% NH4OH to yield (2R)—N′-(3-fluoro-5-(3-methylisoxazol-5-yl)pyridin-2-yl)-2-(5-oxo-1,6-naphthyridin-6(5H)-yl)propanehydrazide (4.927 g, 77% yield).

Workup

concentrationThe crude material was concentrated onto silica gel
custompurified via MPLC
washeluting with 100% DCM to 90% DCM

Sources & evidence

ORD record: ord-78f6f24d866d479dba320120ada07ff6
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08198448B2

Reaction notes

Loading…