Acetonitrile → HCID 58997000, compound

HRID 251206Notes

Reaction equation

HRID 251206 reaction equation
S([O-])(=O)(=O)C.[N:6]1[C:15]2[CH:14]([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][N:21]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:13][CH2:12][CH2:11][C:10]=2[CH:9]=[CH:8][CH:7]=1.[CH3:32][C:33]#[N:34]>CCN(C(C)C)C(C)C>[N:34]1[C:13]([CH2:14][N:16]([CH:14]2[C:15]3[N:6]=[CH:7][CH:8]=[CH:9][C:10]=3[CH2:11][CH2:12][CH2:13]2)[CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])=[CH:12][CH:11]=[CH:32][C:33]=1[C:7]1[CH:8]=[CH:9][CH:10]=[CH:15][N:6]=1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 85257MethanesulfonateHCID 589971372-[4-(5,6,7,8-Tetrahydroquinolin-8-ylamino)-butyl]-isoindole-1,3-dione

Product 1

HCID 58997000HCID 58997000, compound

Reagents, catalysts & solvents 1

HCID 81531DiisopropylethylamineSolvent

Procedure

Using the general alkylation procedure A: Reaction of the mesylate from above and 2-[4-(5,6,7,8-tetrahydro-quinolin-8-ylamino)-butyl]-isoindole-1,3-dione in dry CH3CN and DIPEA gave the desired amine as a yellow oil. Deprotection with hydrazine following General Procedure E gave COMPOUND 361 as a colorless oil. 1H NMR (CDCl3) δ 1.42-1.58 (m, 4H), 1.63-1.72 (m, 1H), 1.86-2.04 (m, 2H), 2.14-2.19 (m, 1H), 2.08-2.19 (m, 2H), 2.60 (t, 2H, J=6.9 Hz), 2.65-2.90 (m, 4H), 3.83 (d, 1H, J=15.6 Hz), 3.99 (d, 1H, J=13.2 Hz), 4.18 (dd, 1H, J=9, 6 Hz), 7.03 (dd, 1H, J=7.8, 4.8 Hz), 7.25-7.33 (m, 2H), 7.74-7.82 (m, 3H), 8.15 (d, 1H, J=8.1 Hz), 8.34 (d, 1H, J=8.1 Hz), 8.51 (d, 1H, J=3.6 Hz), 8.66 (d, 1H, J=3.6 Hz); 13C NMR (CDCl3) δ 21.83, 26.64, 26.79, 29.72, 31.82, 42.40, 53.27, 58.48, 61.50, 119.30, 121.54, 121.86, 123.30, 123.82, 134.59, 136.81, 137.24, 137.52, 147.58, 149.56, 155.27, 156.91, 158.64, 162.20. ES-MS m/z 388 (M+H). Anal. Calcd. for C24H29N5.1.3CH2Cl2: C, 61.03; H, 6.40; N, 14.06. Found: C, 61.25; H, 6.36; N, 13.98.

Sources & evidence

ORD record
ord-a99f6de2a17e426e8809e60016719b47
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

Loading…