Cesium carbonate → HCID 68683572, compound

HRID 2234335Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[CH:4][C:5]2[N:6]([CH3:20])[C:7](=[O:19])[CH2:8][CH2:9][N:10]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:11]=2[N:12]=1.Br[C:22]1[C:37]([F:38])=[CH:36][C:25]([C:26]([NH:28][CH:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[O:27])=[C:24]([Cl:39])[CH:23]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[Cl:39][C:24]1[CH:23]=[C:22]([NH:1][C:2]2[N:12]=[C:11]3[C:5]([N:6]([CH3:20])[C:7](=[O:19])[CH2:8][CH2:9][N:10]3[CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)=[CH:4][N:3]=2)[C:37]([F:38])=[CH:36][C:25]=1[C:26]([NH:28][CH:29]1[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]1)=[O:27]

Participants

Conditions

Temperature: 103 °C

Procedure

2-amino-9-cyclohexyl-5-methyl-8,9-dihydro-5H-pyrimido[5,4-b][1,4]diazepin-6(7H)-one (Intermediate 263; 100 mg, 0.36 mmol), 4-bromo-2-chloro-5-fluoro-N-(1-methylpiperidin-4-yl)benzamide (Intermediate 262; 133 mg, 0.38 mmol), xantphos (12.61 mg, 0.02 mmol), palladium(II) acetate (163 mg, 0.73 mmol) and caesium carbonate (14.20 mg, 0.04 mmol) were added to dioxane (10 mL) and heated at 103° C. overnight. The resulting solution was filtered and passed through a 5 g SCX-3 column. The obtained yellow foam was triturated with hot ethyl acetate to afford a yellow solid.

Workup

filtrationThe resulting solution was filtered
customThe obtained yellow foam was triturated with hot ethyl acetate
customto afford a yellow solid

Sources & evidence

ORD record: ord-b33f18c40ace444f938d86558ee1b726
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07709471B2

Reaction notes

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