Dimethylformamide → HCID 66920266, compound

HRID 1510096Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][C:21](Br)=[CH:22][CH:23]=3)[N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]=2[O:32][C:33]2[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=2[CH3:40])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:41][N:42](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]([C:16]2[C:24]3[C:19](=[CH:20][C:21]([C:41]#[N:42])=[CH:22][CH:23]=3)[N:18]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:17]=2[O:32][C:33]2[CH:38]=[C:37]([F:39])[CH:36]=[CH:35][C:34]=2[CH3:40])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the compound of step 2 (350 mg, 0.58 mmol), zinc cyanide (135 mg, 1.15 mmol) and tetrakis(triphenylphosphin)palladium(0) (133 mg, 0.12 mmol) in DMF (8 ml) was heated to 80° C. for 1 h. After cooling to room temperature, the mixture was partitioned between water and EA and the aqueous phase extracted with EA. The combined organic layers were dried over sodium sulfate, filtered and concentrated. The residue was purified by preparative HPLC and lyophilized overnight. 151 mg of the title compound were obtained.

Workup

temperatureAfter cooling to room temperature
customthe mixture was partitioned between water and EA
extractionthe aqueous phase extracted with EA
dry with materialThe combined organic layers were dried over sodium sulfate
filtrationfiltered
concentrationconcentrated
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-9dd1ad1521aa4f0585b3330764d0ea6c
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211885B2

Reaction notes

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