Cesium carbonate → HCID 70979494, compound

HRID 1485456Notes

Reaction equation

[CH3:1][C:2]1[N:6]2[C:7]3[CH:26]=[CH:25][C:24](B4OC(C)(C)C(C)(C)O4)=[CH:23][C:8]=3[N:9]([C:13]3[CH:18]=[CH:17][C:16]([S:19]([CH3:22])(=[O:21])=[O:20])=[CH:15][CH:14]=3)[CH2:10][C@@H:11]([CH3:12])[C:5]2=[N:4][N:3]=1.Br[C:37]1[N:38]=[CH:39][C:40]([NH2:43])=[N:41][CH:42]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1[N:6]2[C:7]3[CH:26]=[CH:25][C:24]([C:37]4[N:38]=[CH:39][C:40]([NH2:43])=[N:41][CH:42]=4)=[CH:23][C:8]=3[N:9]([C:13]3[CH:14]=[CH:15][C:16]([S:19]([CH3:22])(=[O:20])=[O:21])=[CH:17][CH:18]=3)[CH2:10][C@@H:11]([CH3:12])[C:5]2=[N:4][N:3]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of (R)-1,4-dimethyl-6-(4-(methylsulfonyl)phenyl)-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine (0.34 mmol) in 1,4-dioxane and H2O (10:1, 5 mL) was added 5-bromopyrazin-2-amine (63.2 mg, 0.36 mmol), Cs2CO3 (197.3 mg, 0.61 mmol) and Tetrakis(triphenylphosphine)palladium(0) (21.9 mg, 0.03 mmol). The mixture was purged with N2 and stirred in the microwave at 130° C. for 20 min. The reaction solution was concentrated and purified by prep-TLC (elute: DCM:CH3OH=15:1) to give (R)-5-(1,4-dimethyl-6-(4-(methylsulfonyl)phenyl)-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-8-yl)pyrazin-2-amine (39 mg, 28%).

Workup

customThe mixture was purged with N2
concentrationThe reaction solution was concentrated
custompurified by prep-TLC (elute: DCM:CH3OH=15:1)

Sources & evidence

ORD record: ord-912e5cc224444e12bc85ad2901d1c41c
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422292B2

Reaction notes

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