Triethylamine; trifluoroacetic acid → N2-[3-Methoxy-4-(2-{1-[4-(quinolin-3-ylamino)-pyrimidin-2-yl]-piperidin-4-yl}-ethoxy)-phenyl]-N4-quinolin-3-yl-pyrimidine-2,4-diamine

HRID 495484Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([NH:8][C:9]2[CH:10]=[N:11][C:12]3[C:17]([CH:18]=2)=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[CH:4][N:3]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([NH2:37])[CH:24]=[CH:25][C:26]=1[O:27][CH2:28][CH2:29][CH:30]1[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]1.[C:38](O)([C:40](F)(F)F)=O.CC[N:47]([CH2:50][CH3:51])[CH2:48][CH3:49]>CS(C)=O>[CH3:19][O:20][C:21]1[CH:22]=[C:23]([NH:37][C:2]2[N:7]=[C:6]([NH:8][C:9]3[CH:10]=[N:11][C:12]4[C:17]([CH:18]=3)=[CH:16][CH:15]=[CH:14][CH:13]=4)[CH:5]=[CH:4][N:3]=2)[CH:24]=[CH:25][C:26]=1[O:27][CH2:28][CH2:29][CH:30]1[CH2:35][CH2:34][N:33]([C:36]2[N:7]=[C:6]([NH:8][C:51]3[CH:50]=[N:47][C:48]4[C:38]([CH:40]=3)=[CH:10][CH:9]=[CH:18][CH:49]=4)[CH:5]=[CH:4][N:3]=2)[CH2:32][CH2:31]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (2-chloro-pyrimidin-4-yl)-quinolin-3-yl-amine (105 mg, 0.41 mmol, 1.0 eq.) and 3-methoxy-4-[2-(1-methyl-piperidin-4-yl)-ethoxy]-phenylamine (Step E, 119 mg, 0.45 mmol, 1.1 eq.) in 0.5 mL of DMSO was added a 1/1 (v/v) mixture of TFA/Et3N (77 μl, 0.41 mmol, 1.0 eq.). The reaction mixture was heated to 100° C. and stirred for 16 h, cooled, concentrated and purified by column chromatography (0-5% MeOH in CH2Cl2 with 1% NH4OH (aq.)). Trituration with CH2Cl2 provided the title compound. MS m/z=691.8 (M+H)+ Calc'd for C40H38N10O2: 690.81.

Workup

temperaturecooled
concentrationconcentrated
custompurified by column chromatography (0-5% MeOH in CH2Cl2 with 1% NH4OH (aq.))

Sources & evidence

ORD record: ord-657c9ec5ef5542109d03fa959c41d06d
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939874B2

Reaction notes

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