Diisopropylethylamine → HCID 67205432, compound

HRID 2041774Notes

Reaction equation

HRID 2041774 reaction equation
Cl.Cl.[C:3]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([N:16]3[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]3)=[CH:13][CH:14]=2)[CH:9]([NH2:22])[CH2:8][CH:7]1[CH3:23])(=[O:5])[CH3:4].CCN(C(C)C)C(C)C.Cl[C:34]1[N:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=1>CN1C(=O)CCC1>[C:3]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([N:16]3[CH:20]=[C:19]([CH3:21])[N:18]=[CH:17]3)=[CH:13][CH:14]=2)[CH:9]([NH:22][C:34]2[N:39]=[CH:38][C:37]([C:40]#[N:41])=[CH:36][CH:35]=2)[CH2:8][CH:7]1[CH3:23])(=[O:5])[CH3:4]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 51520946-Chloro-3-pyridinecarbonitrileHCID 67205778HCID 67205778, compound

Product 1

HCID 67205432HCID 67205432, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 1-acetyl-2-methyl-6-(4-methyl-1H-imidazol-1-yl)-1,2,3,4-tetrahydro-4-quinolinamine di-hydrochloride (for a preparation see intermediate 61) (85 mg, 0.299 mmol) in NMP (2 mL) was treated with DIPEA (0.209 ml, 1.196 mmol), then 6-chloro-3-pyridinecarbonitrile (49.7 mg, 0.359 mmol) and the resulting mixture was heated at 200° C. for 30 min under microwave irradiation, then cooled to room temperature and the solution purified by MDAP to give 6-{[1-acetyl-2-methyl-6-(4-methyl-1H-imidazol-1-yl)-1,2,3,4-tetrahydro-4-quinolinyl]amino}-3-pyridinecarbonitrile (12.2 mg, 0.032 mmol, 11% yield) as a beige solid.

Workup

  1. customthe solution purified by MDAP

Sources & evidence

ORD record
ord-9d1cd89cc25844cb9c62e08f4e687438
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

Loading…