Triethylamine → 2-(4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)naphthalene-1-yl)piperidin-1-yl)acetamide

HRID 2093822Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:30]=[C:29]([CH3:31])[NH:28][N:27]=2)=[N:4][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1.Br[CH2:33][C:34]([NH2:36])=[O:35].C(N(CC)CC)C>CN(C=O)C>[Cl:1][C:2]1[C:3]([NH:25][C:26]2[CH:30]=[C:29]([CH3:31])[NH:28][N:27]=2)=[N:4][C:5]([NH:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([CH:19]3[CH2:24][CH2:23][N:22]([CH2:33][C:34]([NH2:36])=[O:35])[CH2:21][CH2:20]3)=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

A mixture of 5-chloro-N4-(5-methyl-1H-pyrazol-3-yl)-N2-(4-(piperidin-4-yl)naphthalene-1-yl)pyrimidine-2,4-diamine (30.8 mg, 0.07 mmol), 2-bromoacetamide (19.6 mg, 0.14 mmol) and triethylamine (30.0 μL, 0.21 mmol) in 2 mL of DMF was heated at 130° C. in a microwave reactor for 20 min. The crude product was purified by RP-HPLC to afford 2-(4-(4-(5-chloro-4-(5-methyl-1H-pyrazol-3-ylamino)pyrimidin-2-ylamino)naphthalene-1-yl)piperidin-1-yl)acetamide; ESMS m/z 491.2 (M+H+).

Workup

customThe crude product was purified by RP-HPLC

Sources & evidence

ORD record: ord-aed81e2f7564446bae93ac5896561c6b
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08445505B2

Reaction notes

Loading…