Benzenepropanenitrile → HCID 57950620, compound

HRID 598857Notes

Reaction equation

HRID 598857 reaction equation
[C:1]1([CH2:7][CH2:8][C:9]#[N:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:11]([C:18]1[C:19]([C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[CH:36]=[N:35][CH:34]=[CH:33]3)=[N:20][O:21][C:22]=1[NH:23][C:24](=O)OCC=C)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[CH:40]1C2C(=CC(C3C=C(NC(=O)OCC=C)ON=3)=CC=2)C=C[N:41]=1>C(#N)C>[NH2:10][C@@H:9]([CH2:8][C:7]1[C:1]2[C:6](=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:41][CH:40]=1)[CH2:24][NH:23][C:22]1[O:21][N:20]=[C:19]([C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[CH:36]=[N:35][CH:34]=[CH:33]3)[C:18]=1[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 12581BenzenepropanenitrileHCID 57950560HCID 57950560, compoundHCID 67062692HCID 67062692, compound

Product 1

HCID 57950620HCID 57950620, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

This compound was synthesized in an analogous manner to Example 32 but using 3-phenylpropionitrile (commercially available from Acros Organics Order Number 17399) instead of acetonitrile in the preparation of allyl 4-benzyl-3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate according to Scheme 6 instead of allyl 3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate. MS m/z: 474 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.24 (s, 1H), 8.44 (d, J=5.87 Hz, 1H), 8.11 (d, J=8.61 Hz, 1H), 7.93 (s, 1H), 7.75 (dd, J=8.61, 1.37 Hz, 1H), 7.70 (d, J=5.87 Hz, 1H), 7.55 (d, J=7.82 Hz, 1H), 7.39 (d, J=8.02 Hz, 1H), 7.04-7.24 (m, 8H), 3.82 (m, 3H), 3.60-3.73 (m, 2H), 3.21-3.25 (m, 1H), 3.13 (m, 1H).

Workup

  1. customThis compound was synthesized in an analogous manner to Example 32

Sources & evidence

ORD record
ord-2e22dd050fc94727842265095e967aa5
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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