6-((E)-3-Dimethylamino-acryloyl)-3-((S)-3-hydroxy-pyrrolidin-1-yl)-pyridine-2-carbonitrile → US9433622, Dmx-57

HRID 55895Notes

Reaction equation

CN(C)/[CH:3]=[CH:4]/[C:5]([C:7]1[N:12]=[C:11]([C:13]#[N:14])[C:10]([N:15]2[CH2:19][CH2:18][C@H:17]([OH:20])[CH2:16]2)=[CH:9][CH:8]=1)=O.[N:22]1([C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH2:37])=[NH:36])=[CH:30][CH:29]=2)[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>CCO>[OH:20][C@H:17]1[CH2:18][CH2:19][N:15]([C:10]2[C:11]([C:13]#[N:14])=[N:12][C:7]([C:5]3[CH:4]=[CH:3][N:37]=[C:35]([NH:34][C:31]4[CH:30]=[CH:29][C:28]([N:22]5[CH2:27][CH2:26][O:25][CH2:24][CH2:23]5)=[CH:33][CH:32]=4)[N:36]=3)=[CH:8][CH:9]=2)[CH2:16]1

Participants

Conditions

Temperature: 180 °C

Procedure

Compound 66 (150 mg, 0.524 mmol) and N-(4-morpholin-4-yl-phenyl)-guanidine were dissolved in EtOH (4 mL). The mixture was then stirred at 180° C. in the microwave for 30 minutes. The solvent was evaporated in vacuo and the residue diluted with MeOH (50 mL). The solution was heated to 60° C. on a rotary evaporator with swirling. The solution was cooled to rt and the solvent carefully decanted. The process was repeated twice more. The residual solvent was then evaporated in vacuo. The title compound was afforded as a yellow solid (110 mg, 47%); LCMS, Rt=2.58 min (MeOH-FA method), m/z 444 (MH+).

Workup

customThe solvent was evaporated in vacuo
additionthe residue diluted with MeOH (50 mL)
temperatureThe solution was heated to 60° C. on a rotary evaporator
temperatureThe solution was cooled to rt
customthe solvent carefully decanted
customThe residual solvent was then evaporated in vacuo

Sources & evidence

ORD record: ord-8eb1e41093b94ed69e903a32d9389b5b
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09433622B2

Reaction notes

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