Cesium carbonate → HCID 86690929, compound

HRID 714704Notes

Reaction equation

Br[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:15]([F:18])([F:17])[F:16])[N:4]=1.[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:27]([CH2:32][C@H:33]([OH:38])[C:34]([F:37])([F:36])[F:35])[C:28](=[O:31])[NH:29][N:30]=2)=[CH:22][CH:21]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[N:27]([CH2:32][C@H:33]([OH:38])[C:34]([F:36])([F:37])[F:35])[C:28](=[O:31])[N:29]([CH2:2][C:3]3[CH:8]=[CH:7][N:6]=[C:5]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=4[C:15]([F:18])([F:17])[F:16])[N:4]=3)[N:30]=2)=[CH:22][CH:21]=1

Participants

Conditions

Temperature: 60 °C

Procedure

303 mg (0.19 mmol) of the compound from Example 80A (purity about 20%) were dissolved in 2 ml of acetonitrile, and 65 mg (0.21 mmol) of the compound from Example 5A and 93 mg (0.29 mmol) of cesium carbonate were added. The mixture was stirred at 60° C. for 2.5 h and at RT for a further 96 h. The solid was then filtered off and rinsed with a little acetonitrile. The filtrate was concentrated under reduced pressure and directly purified chromatographically [Method 19]. This gave 19 mg of the target compound, which were subjected to a further chromatographic purification on silica gel (mobile phase: cyclohexane/ethyl acetate 7:3, then 1:1). This gave 8 mg (7% of theory) of the target compound.

Workup

filtrationThe solid was then filtered off
washrinsed with a little acetonitrile
concentrationThe filtrate was concentrated under reduced pressure
customdirectly purified chromatographically [Method 19]
customThis gave 19 mg of the target compound, which were subjected to a further chromatographic purification on silica gel (mobile phase

Sources & evidence

ORD record: ord-940865425c88472ebacc192c9e1e2f6d
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187466B2

Reaction notes

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