(R)-2-phenyl-2-(pyrrolidin-1-yl)acetic acid → (2S)-1-[(2R)-2-(diethylamino)-2-phenylacetyl]-N-(4-{[(4-fluorophenyl){4-[({(2S)-1-[(2R)-2-phenyl-2-pyrrolidin-1-ylacetyl]pyrrolidin-2-yl}carbonyl)amino]benzyl}amino]methyl}phenyl)pyrrolidine-2-carboxamide

HRID 923407Notes

Reaction equation

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

Participants

Reactant 2

HCID 1091376(R)-2-phenyl-2-(pyrrolidin-1-yl)acetic acid

HCID 59540095(S)-1-((R)-2-(diethylamino)-2-phenylacetyl)-N-(4-(((4-fluorophenyl)(4-((S)-pyrrolidine-2-carboxamido)benzyl)amino)methyl)phenyl)pyrrolidine-2-carboxamide

Product 1

HCID 59540188(2S)-1-[(2R)-2-(diethylamino)-2-phenylacetyl]-N-(4-{[(4-fluorophenyl){4-[({(2S)-1-[(2R)-2-phenyl-2-pyrrolidin-1-ylacetyl]pyrrolidin-2-yl}carbonyl)amino]benzyl}amino]methyl}phenyl)pyrrolidine-2-carboxamideYield 37.4%

Procedure

The product from Example 81A (0.032 g, 0.045 mmol) and (R)-2-phenyl-2-(pyrrolidin-1-yl)acetic acid (0.010 g, 0.05 mmol) were processed as in Example 81A to give 0.015 g (37%) of the title compound as an off-white solid. 1H NMR (500 MHz, DMSO-D6) δ ppm 0.89 (t, J=7.10 Hz, 6 H) 1.56-1.66 (m, 4 H) 1.74-1.88 (m, 4 H) 1.94-2.09 (m, 4 H) 2.29-2.34 (m, 2 H) 2.57-2.62 (m, 4 H) 3.36-3.50 (m, 4 H) 3.75-3.88 (m, 2 H) 4.21 (s, 1 H) 4.31 (dd, J=7.93, 4.27 Hz, 1 H) 4.38 (dd, J=8.16, 4.50 Hz, 1 H) 4.57 (s, 4 H) 4.68 (s, 1 H) 6.65 (dd, J=9.31, 4.43 Hz, 2 H) 6.92 (t, J=8.93 Hz, 2 H) 7.19 (d, J=8.24 Hz, 4 H) 7.26-7.30 (m, 2 H) 7.31-7.36 (m, 4 H) 7.40 (d, J=7.17 Hz, 2 H) 7.46 (d, J=6.87 Hz, 2 H) 7.53 (d, J=8.24 Hz, 4H) 9.96 (d, J=5.34 Hz, 2 H); MS ESI− m/z 890.5.

Sources & evidence

ORD record: ord-acfe9234e6114155a02591ca917281ab
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09278922B2

Reaction notes

Loading…