1,2,3,4-Tetrahydroisoquinoline → HCID 18332646, compound

HRID 2268970Notes

Reaction equation

HRID 2268970 reaction equation
[N+](C1C=CC(O[C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([CH:19]([NH:21][C:22]3[N:27]=[C:26]([N:28]4[C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=5[N:30]=[CH:29]4)[CH:25]=[CH:24][N:23]=3)[CH3:20])[CH2:14]2)=[O:12])=CC=1)([O-])=O.[CH2:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:40][CH2:39][NH:38]1.C[N:48](C1C=CC=CN=1)C>C(Cl)Cl>[CH:37]1([NH:48][C:11]([N:13]2[CH2:18][CH2:17][CH2:16][CH:15]([CH:19]([NH:21][C:22]3[N:27]=[C:26]([N:28]4[C:32]5[CH:33]=[CH:34][CH:35]=[CH:36][C:31]=5[N:30]=[CH:29]4)[CH:25]=[CH:24][N:23]=3)[CH3:20])[CH2:14]2)=[O:12])[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH2:40][CH2:39][NH:38]1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 218852-DimethylaminopyridineHCID 18332639HCID 18332639, compound

Product 1

HCID 18332646HCID 18332646, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[1-(1-(4-nitrophenyl)oxycarbonylpiperidin-3-yl)-ethylamino]-4-[benzimidazol-1-yl]pyrimidine (14.5 mg, 0.03 mmol) in CH2Cl2 (0.5 mL) was added 1,2,3,4-tetrahydroisoquinoline (4.3 gL, 0.033 mmol) followed by a few crystals of dimethylaminopyridine. The reaction mixture was stirred for 4 days, the solvent was removed under reduced pressure, and the crude material was purified by preparative thin layer chromatography eluting with 1:1 acetone:hexane to obtain 4 mg of the title compound. Partial 1H NMR (500 MHz, CDCl3): δ 8.61 (s, 1H); 8.37 (br s, 1H); 8.16 (d, J=7.3 Hz, 1H); 7.86 (d, J=7.3 Hz, 1H); 7.39 m, 2H); 7.15-7.04 (aromatic H's, 4H); 6.78 (d, J=5.5 Hz, 1H); 4.4 (s, 2H); 1.31 (d, J=6.6 Hz, 3H). Mass spectrum 482.4 (LC-MS, M+1).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customthe crude material was purified by preparative thin layer chromatography
  3. washeluting with 1:1 acetone

Sources & evidence

ORD record
ord-5dc6f112c81440859911953834914387
Source dataset
uspto-grants-2001_12
Patent number
US06329380B1

Reaction notes

Loading…