3-Bromopropionitrile → HCID 178447836, compound

HRID 1725187Notes

Reaction equation

HRID 1725187 reaction equation
[C:1]([NH:8][C:9]([NH:11][C:12](=[O:34])[CH2:13][N:14]1[C:18]([CH:19]2[CH2:24][CH2:23][CH:22]([CH2:25][CH2:26][CH3:27])[CH2:21][CH2:20]2)=[CH:17][CH:16]=[C:15]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[NH:10])(OC(C)(C)C)=O.Br[CH2:36][CH2:37][C:38]#[N:39]>CN(C=O)C>[NH2:10]/[C:9](/[NH:8][CH2:1][CH2:36][CH2:37][C:38]#[N:39])=[N:11]\[C:12](=[O:34])[CH2:13][N:14]1[C:18]([C@H:19]2[CH2:20][CH2:21][C@H:22]([CH2:25][CH2:26][CH3:27])[CH2:23][CH2:24]2)=[CH:17][CH:16]=[C:15]1[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 170203-BromopropionitrileHCID 141152040HCID 141152040, compound

Product 1

HCID 178447836HCID 178447836, compoundYield 28.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a 10 mL glass microwave reaction vessel under nitrogen, 17 mg (0.425 mmol) sodium hydride (obtained as a 60% dispersion in mineral oil) was slurried with a solution of 0.133 g (0.28 mmol) N-Boc-N′-{2-[2-phenyl-5-(4-propyl-cyclohexyl)-pyrrol-1-yl]-acetyl}-guanidine from Step 8 in 4 ml anhydrous DMF, and 41 mg (0.28 mmol) 3-bromopropionitrile. The reaction vessel was capped and microwave at 150° C. for 460 sec in a microwave reactor. (Emrys™ Microwave Synthesizer, Personal Chemistry Inc., Foxboro, Mass.) The reaction was concentrated and redissolved in 2 mL CH2Cl2. 0.66 mL trifluoroacetic acid was added and the reactions were shaken for 1 hr. The reactions were then concentrated, redissolved in DMSO:MeCN (4:1) and purified by Gilson preparative 4HPLC to afford 34.5 mg of the title compound [2LC-MS data; molecular ion and retention time): m/z 434 (M+H); 2.77 min] as an oil.

Workup

  1. customThe reaction vessel was capped
  2. concentration(Emrys™ Microwave Synthesizer, Personal Chemistry Inc., Foxboro, Mass.) The reaction was concentrated
  3. dissolutionredissolved in 2 mL CH2Cl2
  4. addition0.66 mL trifluoroacetic acid was added
  5. concentrationThe reactions were then concentrated
  6. dissolutionredissolved in DMSO:MeCN (4:1)
  7. custompurified by Gilson preparative 4HPLC

Sources & evidence

ORD record
ord-fcacb0906e1f43feb49c4e0f79956c84
Source dataset
uspto-grants-2009_02
Patent number
US07488832B2

Reaction notes

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