(2S,4S)-1-[(N-benzyloxycarbonyl-N-[4-(benzotriazol-1-yl)oxycarbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile → HCID 68843182, compound

HRID 227978Notes

Reaction equation

HRID 227978 reaction equation
[CH2:1]([O:8][C:9]([N:11]([CH2:32][C:33]([N:35]1[CH2:39][C@@H:38]([F:40])[CH2:37][C@H:36]1[C:41]#[N:42])=[O:34])[C:12]12[CH2:19][CH2:18][C:15]([C:20](ON3C4C=CC=CC=4N=N3)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:43]([N:45]([CH2:60][CH3:61])[C:46]([C@@H:48]1[CH2:53][CH2:52][CH2:51][N:50]([CH:54]2[CH2:59][CH2:58][NH:57][CH2:56][CH2:55]2)[CH2:49]1)=[O:47])[CH3:44]>>[CH2:1]([O:8][C:9]([N:11]([CH2:32][C:33]([N:35]1[CH2:39][C@@H:38]([F:40])[CH2:37][C@H:36]1[C:41]#[N:42])=[O:34])[C:12]12[CH2:19][CH2:18][C:15]([C:20]([N:57]3[CH2:56][CH2:55][CH:54]([N:50]4[CH2:51][CH2:52][CH2:53][C@@H:48]([C:46](=[O:47])[N:45]([CH2:60][CH3:61])[CH2:43][CH3:44])[CH2:49]4)[CH2:59][CH2:58]3)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 57756828(2S,4S)-1-[(N-benzyloxycarbonyl-N-[4-(benzotriazol-1-yl)oxycarbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrileHCID 68842667HCID 68842667, compound

Product 1

HCID 68843182HCID 68843182, compoundYield 77.8%

Procedure

In a similar manner to Example 4, (2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(benzotriazol-1-yl)oxycarbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (74.9 mg) and (3R)—N,N-diethyl-1-(piperidin-4-yl)piperidine-3-carboxamide (61.0 mg) were used to obtain (2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-[4-[(3R)-3-(N,N-diethylcarbamoyl)piperidin-1-yl]piperidin-1-yl]carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (71.7 mg).

Sources & evidence

ORD record
ord-9f8551b8ae3f460e9c7401e74cb7d44a
Source dataset
uspto-grants-2009_07
Patent number
US07560569B2

Reaction notes

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