Potassium Carbonate → HCID 86727416, compound

HRID 519051Notes

Reaction equation

[CH:1]([N:14]1[CH2:17][C:16]([NH:19][C:20]2[CH:21]=[C:22]3[C:31](=[CH:32][C:33]=2Br)[O:30][CH2:29][C:28]2[N:23]3[CH:24]([CH3:36])[C:25](=[O:35])[NH:26][N:27]=2)([CH3:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:37]([O-])([O-])=O.[K+].[K+].CB1OB(C)OB(C)O1>O.O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:1]([N:14]1[CH2:17][C:16]([NH:19][C:20]2[CH:21]=[C:22]3[C:31](=[CH:32][C:33]=2[CH3:37])[O:30][CH2:29][C:28]2[N:23]3[CH:24]([CH3:36])[C:25](=[O:35])[NH:26][N:27]=2)([CH3:18])[CH2:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.0598 g, 0.073 mmol), 6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-7-bromo-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (Example #79, Step B, 0.20 g, 0.366 mmol), K2CO3 (0.152 g, 1.098 mmol), 2,4,6-trimethyl-1,3,5,2,4,6-trioxatriborinane (0.138 g, 1.098 mmol) in water (1 mL) and dioxane (6 mL) was stirred at 120° C. overnight. The reaction mixture was cooled to ambient temperature and the solvent was removed in vacuo. The residue was purified by preparative HPLC (Table 3, Method 13) to give 6-(1-benzhydryl-3-methyl-azetidin-3-ylamino)-4,7-dimethyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.10 g, 56%). LC/MS (Table 1, Method 2) Rt=0.959 min; MS m/z: 482 [M+H]+.

Workup

temperatureThe reaction mixture was cooled to ambient temperature
customthe solvent was removed in vacuo
customThe residue was purified by preparative HPLC (Table 3, Method 13)

Sources & evidence

ORD record: ord-a382b23926bf4d648bc96e0cfec10100
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115151B2

Reaction notes

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