Acetonitrile → HCID 57950690, compound

HRID 598858Notes

Reaction equation

HRID 598858 reaction equation
[CH3:1][CH:2]([CH3:7])[CH2:3][CH2:4][C:5]#[N:6].[CH2:8]([C:12]1[C:13]([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[CH:30]=[N:29][CH:28]=[CH:27]3)=[N:14][O:15][C:16]=1[NH:17][C:18](=O)OCC=C)[CH:9]([CH3:11])[CH3:10].C1C2[C:38](=CC(C3C=C(NC(=O)OCC=C)ON=3)=CC=2)[CH:37]=[CH:36]N=1.[C:56](#[N:58])C>>[NH2:6][C@@H:5]([CH2:4][C:3]1[C:2]2[C:7](=[CH:36][CH:37]=[CH:38][CH:1]=2)[NH:58][CH:56]=1)[CH2:18][NH:17][C:16]1[O:15][N:14]=[C:13]([C:24]2[CH:25]=[C:26]3[C:31](=[CH:32][CH:33]=2)[CH:30]=[N:29][CH:28]=[CH:27]3)[C:12]=1[CH2:8][CH:9]([CH3:11])[CH3:10]

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 10956Pentanenitrile, 4-methyl-HCID 57950560Allyl 3-(isoquinolin-6-yl)isoxazol-5-ylcarbamateHCID 67062702HCID 67062702, compound

Product 1

HCID 57950690HCID 57950690, compound

Procedure

This compound was synthesized in an analogous manner to Example 32 but using 4-methylpentanenitrile (commercially available from TCI America Organic Chemicals Order Number M0458) instead of acetonitrile in the preparation of allyl 4-isobutyl-3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate according to Scheme 6 instead of allyl 3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate. MS m/z: 440 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.73 (s, 1H), 8.61 (d, J=6.65 Hz, 1H), 8.53-8.57 (m, 1H), 8.43 (s, 2H), 8.15 (dd, J=8.61, 1.56 Hz, 1H), 0.57 (d, J=7.43 Hz, 1H), 7.40 (d, J=8.22 Hz, 1H), 7.25 (s, 1H), 7.15 (t, J=7.43 Hz, 1H), 7.06 (t, J=7.24 Hz, 1H), 3.78-3.83 (m, 1H), 3.63-3.68 (m, 2H), 3.22-3.28 (m, 1H), 3.10-3.16 (m, 1H), 2.37 (d, J=7.43 Hz, 2H), 1.58 (dt, J=13.60, 6.70 Hz, 1H), 0.76 (d, J=6.65 Hz, 6H).

Workup

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

Sources & evidence

ORD record
ord-bd1a47be0fd64aada0e0f3000c474a6d
Source dataset
uspto-grants-2011_03
Patent number
US07897619B2

Reaction notes

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