Diisobutylaluminum hydride → HCID 58798988, compound

HRID 2117104Notes

Reaction equation

[F:1][C:2]1[CH:23]=[C:22]([NH:24][C:25](=[O:37])[CH2:26][C:27]([NH:29][C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)=[O:28])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:19])[C:12]([C:14](OCC)=[O:15])=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1.CC(C[AlH]CC(C)C)C>C1COCC1>[F:1][C:2]1[CH:23]=[C:22]([NH:24][C:25](=[O:37])[CH2:26][C:27]([NH:29][C:30]2[CH:31]=[CH:32][C:33]([F:36])=[CH:34][CH:35]=2)=[O:28])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[C:10]2=[C:11]([CH3:19])[C:12]([CH2:14][OH:15])=[CH:13][N:9]2[N:8]=[CH:7][N:6]=1

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of ethyl 4-(2-fluoro-4-(3-(4-fluorophenylamino)-3-oxopropanamido)phenoxy)-5-methylpyrrolo[2,1-f][1,2,4]triazine-6-carboxylate (66 mg, 0.13 mmol, Example 40) in 20 mL of THF at −78° C. was added DIBAL-H (1 M, 1.65 mL). The reaction mixture was allowed to stir at −78° C. for 1 h and then at room temperature for 2 h. At that time, HPLC analysis indicated the completion of the reaction. The reaction was quenched with 4 mL of MeOH, followed by addition of 4 mL of H2O. The mixture was allowed to stir for 0.5 h and then Na2SO4 was added. The stirring was continued for 1 h. Filtration and concentration gave rise to the title compound (50 mg, 82%). 1H NMR (CD3OD) δ 7.70 (m, 3H), 7.50 (m, 2H), 7.25 (m, 2H), 7.00 (m, 2H), 4.60 (s, 2H), 3.45 (s, 2H), 2.50 (s, 3H); MS(ESI+) m/z 468.2 (M+H)+.

Workup

waitat room temperature for 2 h
customthe completion of the reaction
customThe reaction was quenched with 4 mL of MeOH
additionfollowed by addition of 4 mL of H2O
stirringto stir for 0.5 h
additionNa2SO4 was added
waitThe stirring was continued for 1 h
filtrationFiltration and concentration

Sources & evidence

ORD record: ord-32e403629c684034b310fb1717b46c11
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07439246B2

Reaction notes

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