Sodium Cyanide → HCID 86695193, compound

HRID 1504033Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[CH2:18][CH2:17][C:16]2[S:15][C:14]3[N:13]=[CH:12][N:11]=[C:10]([O:19][CH:20]4[CH2:25][CH2:24][CH:23]([N:26]5[CH2:31][CH2:30][NH:29][C:28](=[O:32])[CH2:27]5)[CH2:22][CH2:21]4)[C:9]=3[C:8]1=2)(=O)=O.[C-:33]#[N:34].[Na+]>CS(C)=O.CN(C1C=CN=CC=1)C.C(Cl)Cl>[O:32]=[C:28]1[NH:29][CH2:30][CH2:31][N:26]([CH:23]2[CH2:24][CH2:25][CH:20]([O:19][C:10]3[C:9]4[C:8]5[C@@H:7]([CH2:6][C:33]#[N:34])[CH2:18][CH2:17][C:16]=5[S:15][C:14]=4[N:13]=[CH:12][N:11]=3)[CH2:21][CH2:22]2)[CH2:27]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of [(3S)-12-[[4-(3-oxopiperazin-1-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]methyl methanesulfonate (450 mg, 0.94 mmol, 1.00 equiv) in DMSO (10 mL) was added NaCN (276 mg, 5.63 mmol, 6.00 equiv) and DMAP (11 mg, 0.094 mmol, 0.10 equiv) at room temperature. The resulting solution was stirred for 2 h at 80° C. After cooling to r.t, the resulting solution was diluted with DCM (100 mL), washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified by column chromatography on silica gel with DCM/MeOH (10:1) to afford 330 mg (86%) of 2-[(3R)-12-[[4-(3-oxopiperazin-1-yl)cyclohexyl]oxy]-7-thia-9,11-diazatricyclo[6.4.0.0[2,6]]dodeca-1(8),2(6),9,11-tetraen-3-yl]acetonitrile as a yellow solid.

Workup

temperatureAfter cooling
washwashed with brine
dry with materialdried over anhydrous sodium sulfate
concentrationconcentrated under vacuum
customThe residue was purified by column chromatography on silica gel with DCM/MeOH (10:1)

Sources & evidence

ORD record: ord-89e63615f76d4745b754ce83911d3fe3
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212190B2

Reaction notes

Loading…