Benzeneethanamine, alpha-methyl-, phosphate (1:1) → HCID 45254328, compound

HRID 1970407Notes

Reaction equation

Cl[C:2]1[N:7]=[CH:6][C:5]2[O:8][C:9]3[C:14]([C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:4]=2[CH:3]=1)=[CH:13][C:12]([C:21]1[CH:22]=[N:23][CH:24]=[N:25][CH:26]=1)=[CH:11][CH:10]=3.[CH3:27][C:28]([CH3:41])([CH3:40])/[CH:29]=[CH:30]/B1OC(C)(C)C(C)(C)O1.CC(N)CC1C=CC=CC=1.OP(O)(O)=O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O>[CH3:27][C:28]([CH3:41])([CH3:40])/[CH:29]=[CH:30]/[C:2]1[N:7]=[CH:6][C:5]2[O:8][C:9]3[C:14]([C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:4]=2[CH:3]=1)=[CH:13][C:12]([C:21]1[CH:26]=[N:25][CH:24]=[N:23][CH:22]=1)=[CH:11][CH:10]=3

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of (S)-3-chloro-7-(pyrimidin-5-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (0.967 g, 2.64 mmol), trans-(3,3-dimethylbutenyl)boronic acid pinacol ester (1.389 g, 6.61 mmol), AmPhos (0.094 g, 0.132 mmol), and potassium phosphate hydrate (1.218 g, 5.29 mmol) in 10 mL dioxane/water (1:1) was heated in the microwave at 130° C. for 1 h. After cooling to rt, the reaction was concentrated and the residue purified by silica gel chromatography using 0-5% MeOH/DCM to give (S,E)-3-(3,3-dimethylbut-1-enyl)-7-(pyrimidin-5-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine. Found MS: MH+=414.

Workup

temperatureAfter cooling to rt
concentrationthe reaction was concentrated
customthe residue purified by silica gel chromatography

Sources & evidence

ORD record: ord-3168c5754b0140df92384e5853fc2cbb
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426447B2

Reaction notes

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