L-Proline → HCID 66620681, compound

HRID 71883Notes

Reaction equation

HRID 71883 reaction equation
[CH3:1][O:2][C:3](=[O:63])[NH:4][CH:5]([C:9]([N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[C:16]1[NH:17][C:18]([C:21]2[CH:33]=[CH:32][C:31]3[C:30]4[C:25](=[CH:26][C:27]([C:34]5[CH:60]=[CH:59][C:37]6[N:38]=[C:39]([CH:41]7[CH:46]8[CH2:47][CH:43]([CH2:44][CH2:45]8)[N:42]7[C:48](=[O:58])[CH:49]([NH:53][C:54]([O:56][CH3:57])=[O:55])[CH:50]([CH3:52])[CH3:51])[NH:40][C:36]=6[CH:35]=5)=[CH:28][CH:29]=4)[C:24]([F:62])([F:61])[C:23]=3[CH:22]=2)=[CH:19][N:20]=1)=[O:10])[CH:6]([CH3:8])[CH3:7].[NH:64]1CCC[C@H:65]1C(O)=O.C(C1CN[C@H](C(O)=O)C1)#N>>[CH3:57][O:56][C:54](=[O:55])[NH:53][CH:49]([C:48]([N:42]1[CH:41]([C:39]2[NH:40][C:36]3[CH:35]=[C:34]([C:27]4[CH:28]=[CH:29][C:30]5[C:31]6[C:23](=[CH:22][C:21]([C:18]7[NH:17][C:16]([CH:12]8[CH2:13][CH:14]([C:65]#[N:64])[CH2:15][N:11]8[C:9](=[O:10])[CH:5]([NH:4][C:3]([O:2][CH3:1])=[O:63])[CH:6]([CH3:7])[CH3:8])=[N:20][CH:19]=7)=[CH:33][CH:32]=6)[C:24]([F:62])([F:61])[C:25]=5[CH:26]=4)[CH:60]=[CH:59][C:37]=3[N:38]=2)[CH:46]2[CH2:47][CH:43]1[CH2:44][CH2:45]2)=[O:58])[CH:50]([CH3:52])[CH3:51]

Participants

4

Reactant 3

HCID 145742L-ProlineHCID 57263372HCID 57263372, compoundHCID 66620162(1-{2-[5-(9,9-Difluoro-7-{2-[2-(2-methoxycarbonylamino-3-methyl-butyryl)-2-aza-bicyclo[2.2.1]hept-3-yl]-3H-benzoimidazol-5-yl]-9H-fluoren-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester

Product 1

HCID 66620681HCID 66620681, compound

Procedure

was prepared in a similar fashion to (1-{2-[5-(9,9-Difluoro-7-{2-[2-(2-methoxycarbonylamino-3-methyl-butyryl)-2-aza-bicyclo[2.2.1]hept-3-yl]-3H-benzoimidazol-5-yl}-9H-fluoren-2-yl)-1H-imidazol-2-yl]-pyrrolidine-1-carbonyl}-2-methyl-propyl)-carbamic acid methyl ester (Example DK), replacing the proline derivative with the corresponding 4-cyano-proline derivative.

Sources & evidence

ORD record
ord-5b576aff3e9d41dbb5bf22e1c542ff87
Source dataset
uspto-grants-2014_09
Patent number
US08822430B2

Reaction notes

Loading…