3-Chloroaniline → HCID 90053335, compound

HRID 2284777Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:12]#[C:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:31])[C@@H:19]([N:21]([CH3:30])[C:22](=[O:29])/[CH:23]=[CH:24]/[CH2:25][N:26]([CH3:28])[CH3:27])[CH3:20])=[CH:4][N:3]=1.[Cl:32][C:33]1[CH:34]=[C:35]([CH:37]=[CH:38][CH:39]=1)[NH2:36].[C@]12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O.C(NCC)C>O1CCCC1>[Cl:32][C:33]1[CH:34]=[C:35]([NH:36][C:2]2[N:7]=[C:6]([NH:8][CH2:9][CH2:10][CH3:11])[C:5]([C:12]#[C:13][CH2:14][CH2:15][CH2:16][NH:17][C:18](=[O:31])[C@@H:19]([N:21]([CH3:30])[C:22](=[O:29])/[CH:23]=[CH:24]/[CH2:25][N:26]([CH3:28])[CH3:27])[CH3:20])=[CH:4][N:3]=2)[CH:37]=[CH:38][CH:39]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of (S,E)-N-(1-((5-(2-chloro-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)-4-(dimethylamino)-N-methyl-2-butenamide (L4, 20 mg) and 3-chloroaniline (28 mg) in tetrahydrofuran (3 mL), (1S)-(+)-10-camphorsulfonic acid (52 mg) was added at room temperature, and the mixture was stirred at 70° C. for 2 hours. The reaction mixture was cooled to room temperature, and then diethylamine was added until the mixture became basic. The solvent was evaporated under reduced pressure, and the obtained residue was purified by basic silica gel column chromatography to obtain (S,E)-N-(1-((5-(2-((3-chlorophenyl)amino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-1-oxopropan-2-yl)-4-(dimethylamino)-N-methyl-2-butenamide (12-2, 4 mg).

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe solvent was evaporated under reduced pressure
customthe obtained residue was purified by basic silica gel column chromatography

Sources & evidence

ORD record: ord-e1b4d8c297594d379c16c6ed8aac0b32
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145415B2

Reaction notes

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