Dimethylformamide → HCID 86630205, compound

HRID 1803818Notes

Reaction equation

HRID 1803818 reaction equation
CN(C=O)C.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:61]2[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][CH:62]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[NH:15][S:16]([C:19]2[S:20][C:21]3[CH:27]=[C:26]([O:28][CH2:29][C:30]4[N:31]=[N:32][N:33]([CH2:35][C:36]([NH:38][C@H:39]([CH2:45][S:46][CH2:47][C:48]5[CH:53]=[CH:52][CH:51]=[C:50]([OH:54])[CH:49]=5)[C:40]([O:42][CH2:43][CH3:44])=[O:41])=[O:37])[CH:34]=4)[CH:25]=[CH:24][C:22]=3[N:23]=2)(=[O:18])=[O:17])=[CH:10][CH:9]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:76][C:77]#[CH:78]>O>[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:61]2[CH:66]=[CH:65][C:64]([O:67][CH3:68])=[CH:63][CH:62]=2)([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)[NH:15][S:16]([C:19]2[S:20][C:21]3[CH:27]=[C:26]([O:28][CH2:29][C:30]4[N:31]=[N:32][N:33]([CH2:35][C:36]([NH:38][C@H:39]([CH2:45][S:46][CH2:47][C:48]5[CH:53]=[CH:52][CH:51]=[C:50]([O:54][CH2:78][C:77]#[CH:76])[CH:49]=5)[C:40]([O:42][CH2:43][CH3:44])=[O:41])=[O:37])[CH:34]=4)[CH:25]=[CH:24][C:22]=3[N:23]=2)(=[O:18])=[O:17])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 86630206HCID 86630206, compound

Product 1

HCID 86630205HCID 86630205, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a 10 mL round bottomed flask equipped with a magnetic stir bar, rubber septum and argon inlet containing DMF (0.5 mL) was placed 134 (49 mg, 0.054 mmol). To this solution K2CO3 (22 mg, 0.162 mmol) and 3-bromoprop-1-yne (0.01 mL, 0.0702 mmol) were added and the reaction was allowed to stir at 60° C. for 12 h. The reaction was then poured into water (50 mL) and extracted into EtOAc (3×20 mL). The combined organic extracts were washed with water (20 mL), brine (20 mL), dried over MgSO4 and concentrated in vacuo used for next step without further purification.

Workup

  1. customTo a 10 mL round bottomed flask equipped with a magnetic stir bar
  2. extractionextracted into EtOAc (3×20 mL)
  3. washThe combined organic extracts were washed with water (20 mL), brine (20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customused for next step without further purification

Sources & evidence

ORD record
ord-c677ff53640e4beeb75c1a0748443586
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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