Cesium carbonate → HCID 68992282, compound

HRID 69462Notes

Reaction equation

[O:1]1[C:5]2([CH2:9][CH2:8][N:7]([C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:25][CH2:24][C:23]5[C:18](=[CH:19][CH:20]=[C:21]([OH:26])[CH:22]=5)[C:17]4=[O:27])=[CH:12][C:11]=3[F:28])[CH2:6]2)[O:4][CH2:3][CH2:2]1.CS([CH2:33][C@@H:34]1[CH2:38][CH2:37][CH2:36][O:35]1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C.O>[O:4]1[C:5]2([CH2:9][CH2:8][N:7]([C:10]3[CH:15]=[CH:14][C:13]([N:16]4[CH2:25][CH2:24][C:23]5[C:18](=[CH:19][CH:20]=[C:21]([O:26][CH2:33][C@@H:34]6[CH2:38][CH2:37][CH2:36][O:35]6)[CH:22]=5)[C:17]4=[O:27])=[CH:12][C:11]=3[F:28])[CH2:6]2)[O:1][CH2:2][CH2:3]1

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 2-[4-(1,4-dioxa-7-aza-spiro[4.4]non-7-yl)-3-fluorophenyl]-6-hydroxy-3,4-dihydro-2H-isoquinolin-1-one (6.9 g), (S)-2-methanesulfonylmethyl-tetrahydrofuran (3.9 g) and cesium carbonate (17.6 g) in DMF (81.6 mL) was heated overnight at 75° C. Then the reaction mixture was diluted with ethyl acetate and water. The organic phase was washed several times with water, dried over sodium sulfate and the solvent was removed in vacuum. In this way the product was obtained with molecular weight 468.53 (C26H29FN2O5); MS (ESI): 469 (M+H+).

Workup

washThe organic phase was washed several times with water
dry with materialdried over sodium sulfate
customthe solvent was removed in vacuum
customIn this way the product was obtained with molecular weight 468.53 (C26H29FN2O5)

Sources & evidence

ORD record: ord-44f8eafca076464e8a27cb328f1a524d
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822495B2

Reaction notes

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