Benzylamine → HCID 11427725, compound
Reaction equation
CCOP(O/[N:10]=[C:11](/[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)\C#N)(OCC)=S.C(N(C(C)C)CC)(C)C.[CH3:29][C:30]1[N:35]=[CH:34][C:33]([C:36]([N:38]2[CH2:42][CH2:41][C@@H:40]([NH2:43])[CH2:39]2)=[O:37])=[CH:32][CH:31]=1.C(N)C1C=CC=CC=1.[N-]=[C:53]=[O:54]>>[CH2:11]([NH:10][C:53]([NH:43][C@@H:40]1[CH2:41][CH2:42][N:38]([C:36]([C:33]2[CH:34]=[N:35][C:30]([CH3:29])=[CH:31][CH:32]=2)=[O:37])[CH2:39]1)=[O:54])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1Participants
Procedure
Phoxime resin (Aldrich Chemical Co.) (0.077 g, 0.14 mmol) was added to a glass reaction vessel and treated with diisopropylethylamine (0.016 g, 0.12 mmol, in 0.75 mL of methylene chloride) and (3R)-1-[(6-methylpyridin-3-yl)carbonyl]pyrrolidin-3-amine (0.013 g, 0.06 mmol, in 1.3 mL of methylene chloride). The mixture was shaken for 18 hours at room temperature to afford a resin-bound oximecarbamate intermediate that was washed with methylene chloride (3 mL). Benzylamine (0.14 mmol, in 0.6 mL of toluene) and diisopropylethylamine (0.14 mmol, in 0.75 mL of toluene) were added to the resin which was then heated to 80° C. and shaken for 18 hours. The reaction mixture was filtered and the filtrate was treated with PS-isocyanate resin (Argonaut Technologies, 0.148 g, 0.18 mmol) for 4 hours at room temperature to remove unreacted benzylamine. The product was separated from the resin by filtration and purified by HPLC as described above.
Workup
- customto afford a resin-bound oximecarbamate intermediate
- washthat was washed with methylene chloride (3 mL)
- temperaturewas then heated to 80° C.
- stirringshaken for 18 hours
- filtrationThe reaction mixture was filtered
- customto remove unreacted benzylamine
- customThe product was separated from the resin by filtration
- custompurified by HPLC
Sources & evidence
- ORD record
- ord-3eb7e4d080ce493b8f43301a18f5feb3
- Source dataset
- uspto-grants-2009_09
- Patent number
- US07592466B2
Reaction notes
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