3-Chloroaniline → HCID 67516744, compound

HRID 61400Notes

Reaction equation

Cl.Cl.Cl.[NH2:4][C@:5]1([C:28]([OH:30])=[O:29])[C@@H:9]([CH2:10][CH2:11][CH2:12][B:13]([OH:15])[OH:14])[CH2:8][N:7]([CH2:16][CH:17]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:27])[CH:24]=3)[CH2:19][NH:18]2)[CH2:6]1.ClC1C=C(N)C=CC=1>>[NH2:4][C@:5]1([C:28]([OH:30])=[O:29])[C@@H:9]([CH2:10][CH2:11][CH2:12][B:13]([OH:14])[OH:15])[CH2:8][N:7]([CH2:16][CH:17]2[CH2:26][C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:27])[CH:24]=3)[CH2:19][NH:18]2)[CH2:6]1

Participants

Reactant 2

HCID 79323-Chloroaniline

HCID 67516743(3R,4S)-3-amino-4-(3-boronopropyl)-1-((6-chloro-1,2,3,4-tetrahydroisoquinolin-3-yl)methyl)pyrrolidine-3-carboxylic acid trihydrochloride

Product 1

HCID 67516744HCID 67516744, compound

Procedure

(3R,4S)-3-amino-4-(3-boronopropyl)-1-((6-chloro-1,2,3,4-tetrahydroisoquinolin-3-yl)methyl)pyrrolidine-3-carboxylic acid trihydrochloride (mixture of two diastereomers, each a racemate) is prepared in a manner analogous to that set forth in Example 49, except 3-chlorophenylamine is used in place of 4-chlorophenylalanine in Step 1. 1H NMR (0.1M DCl in D2O, 400 MHz) δ 7.23 (m, 2 H), 7.09 (m, 1 H), 4.37 (s, 2 H), 4.00 (m, 3 H), 3.82 (m, 2 H), 3.69 (m, 1 H), 3.43 (m, 1 H), 3.22 (m, 1 H), 3.00 (m, 1 H), 2.68 (m, 1 H), 1.60 (m, 1 H), 1.26 (m, 3 H), 0.66 (m, 2 H). ESI+ MS found for C18H27BClN3O4 m/z 378.1 (M−18+H), 360.0 (M−36+H); ESI−MS m/z 376.1 (M−18−H).

Sources & evidence

ORD record: ord-1cf1d9f8c91d44618984fe9f1622a04d
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09440995B2

Reaction notes

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