(3S)-pyrrolidin-3-ol → (1E,4E)-2-amino-N-(3-hydroxypropyl)-8-(4-((S)-3-hydroxypyrrolidine-1-carbonyl)phenyl)-N-propyl-3H-benzo[b]azepine-4-carboxamide

HRID 38020

Reaction equation

HRID 38020 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2=[C:6]([CH:37]=1)[N:7]=[C:8]([NH:29]C(=O)OC(C)(C)C)[CH2:9][C:10]([C:12](=[O:28])[N:13]([CH2:17][CH2:18][CH2:19][O:20][Si](C(C)(C)C)(C)C)[CH2:14][CH2:15][CH3:16])=[CH:11]2.[OH:38][C@H:39]1[CH2:43][CH2:42][N:41]([C:44]([C:46]2[CH:51]=[CH:50][C:49](B3OC(C)(C)C(C)(C)O3)=[CH:48][CH:47]=2)=[O:45])[CH2:40]1.CC1(C)C(C)(C)OB(C2C=CC(C(O)=O)=CC=2)O1.N1CC[C@H](O)C1>>[NH2:29][C:8]1[CH2:9][C:10]([C:12]([N:13]([CH2:17][CH2:18][CH2:19][OH:20])[CH2:14][CH2:15][CH3:16])=[O:28])=[CH:11][C:5]2[CH:4]=[CH:3][C:2]([C:49]3[CH:48]=[CH:47][C:46]([C:44]([N:41]4[CH2:42][CH2:43][C@H:39]([OH:38])[CH2:40]4)=[O:45])=[CH:51][CH:50]=3)=[CH:37][C:6]=2[N:7]=1

Participants

5

Reactant 4

HCID 2733874(3S)-pyrrolidin-3-olHCID 27346214-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acidHCID 66960471(S)-(3-hydroxypyrrolidin-1-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanoneHCID 86652684tert-butyl (1E,4E)-8-bromo-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-3H-benzo[b]azepin-2-ylcarbamate

Product 1

HCID 51034285(1E,4E)-2-amino-N-(3-hydroxypropyl)-8-(4-((S)-3-hydroxypyrrolidine-1-carbonyl)phenyl)-N-propyl-3H-benzo[b]azepine-4-carboxamide

Procedure

The title compound was prepared by the procedure as described in Example 124 (Step F) using tert-butyl (1E,4E)-8-bromo-4-((3-(tert-butyldimethylsilyloxy)propyl)(propyl)carbamoyl)-3H-benzo[b]azepin-2-ylcarbamate and (S)-(3-hydroxypyrrolidin-1-yl)(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methanone that was prepared by the procedure as described in Example 101 (Step H) using 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoic acid and (S)-pyrrolidin-3-ol. MS APCI (+) m/z 705 (M+1) detected.

Workup

  1. customwas prepared by the procedure

Sources & evidence

ORD record
ord-9a7757af39854597b1bd5f58c159b0aa
Source dataset
uspto-grants-2013_09
Patent number
US08524702B2

Linked notes

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