Benzonitrile, 4-bromo- → HCID 57968593, compound

HRID 882760Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=1.[C:10]([O:14][C:15]([N:17]1[CH2:21][C@H:20]([OH:22])[CH2:19][C@@H:18]1[C:23]([N:25]1[CH2:31][CH2:30][CH2:29][N:28]([CH:32]2[CH2:35][CH2:34][CH2:33]2)[CH2:27][CH2:26]1)=[O:24])=[O:16])([CH3:13])([CH3:12])[CH3:11]>>[C:10]([O:14][C:15]([N:17]1[CH2:21][C@H:20]([O:22][C:2]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][CH:3]=2)[CH2:19][C@@H:18]1[C:23]([N:25]1[CH2:31][CH2:30][CH2:29][N:28]([CH:32]2[CH2:33][CH2:34][CH2:35]2)[CH2:27][CH2:26]1)=[O:24])=[O:16])([CH3:13])([CH3:11])[CH3:12]

Participants

Reactant 2

HCID 12162Benzonitrile, 4-bromo-

HCID 44600050HCID 44600050, compound

Product 1

HCID 57968593HCID 57968593, compound

Procedure

The title compound was prepared from 4-bromobenzonitrile and (2R,4R)-2-(4-cyclobutyl-[1,4]diazepane-1-carbonyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester as described for Example 59. MS (ESI): mass calcd. for C26H36N4O4, 468.27; m/z found, 469.4 [M+H]+. 1H NMR (CDCl3): 7.66-7.51 (m, 2H), 6.99-6.86 (m, 2H), 5.05-4.85 (m, 1H), 4.79-4.54 (m, 1H), 4.12-3.96 (m, 1H), 3.84-3.41 (m, 4H), 2.93-2.77 (m, 1H), 2.75-2.13 (m, 5H), 2.10-1.54 (m, 10H), 1.50-1.40 (m, 9H).

Sources & evidence

ORD record: ord-752ef6c5d3c14b7da82af47dca957129
Source dataset: uspto-grants-2012_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08236792B2

Reaction notes

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