Cesium carbonate → HCID 86685842, compound

HRID 1045808Notes

Reaction equation

[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][C@:9]1([CH3:44])[CH2:13][C@@H:12]([C:14]([N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[N:26]([C:27]4[CH:32]=[CH:31][C:30]([F:33])=[C:29]([Cl:34])[CH:28]=4)[N:25]=[C:24]([CH3:35])[CH:23]=3)[CH2:18][CH2:17]2)=[O:15])[C@H:11]([C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=2[F:43])[CH2:10]1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:52][CH2:53][O:54][CH2:55][CH2:56]I>CC(N(C)C)=O>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[Cl:34][C:29]1[CH:28]=[C:27]([N:26]2[C:22]([CH:19]3[CH2:18][CH2:17][N:16]([C:14]([C@@H:12]4[CH2:13][C@@:9]([CH3:44])([N:8]5[CH2:56][CH2:55][O:54][CH2:53][CH2:52]5)[CH2:10][C@H:11]4[C:36]4[CH:41]=[CH:40][C:39]([F:42])=[CH:38][C:37]=4[F:43])=[O:15])[CH2:21][CH2:20]3)=[CH:23][C:24]([CH3:35])=[N:25]2)[CH:32]=[CH:31][C:30]=1[F:33]

Participants

Conditions

Temperature: 110 °C

Procedure

The product from Example 6 (17.2 mg, 0.027 mmol) in DMA (1 mL) was treated with cesium carbonate (63.3 mg, 0.194 mmol) and 2-iodoethyl ether (15.8 mg, 0.049 mmol) at rt. The mixture was heated at 110° C. for 16 h, then cooled to rt and filtered. The filtrate was directly purified by RP-HPLC (15 to 100% acetonitrile/water+0.05% TFA) to afford the title compound. HPLC/MS: 601.4/603.4 (M+1); Rt=2.92 min (LC4).

Workup

temperaturecooled to rt
filtrationfiltered
customThe filtrate was directly purified by RP-HPLC (15 to 100% acetonitrile/water+0.05% TFA)

Sources & evidence

ORD record: ord-6c2aedd0aa7d495995978a070dbd9480
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08569299B2

Reaction notes

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