Triethylamine; trifluoroacetic acid → 3-{2-Methoxy-4-[4-(quinolin-3-ylamino)-pyrimidin-2-ylamino]-phenyl}-1-pyrrolidin-1-yl-propanone

HRID 495480Notes

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.[NH2:19][C:20]1[CH:25]=[CH:24][C:23]([CH2:26][CH2:27][C:28]([N:30]2[CH2:34][CH2:33][CH2:32][CH2:31]2)=O)=[C:22]([O:35][CH3:36])[CH:21]=1.C(O)(C(F)(F)F)=[O:38].CCN(CC)CC>CS(C)=O>[CH3:36][O:35][C:22]1[CH:21]=[C:20]([NH:19][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:25]=[CH:24][C:23]=1[CH2:26][C:27](=[O:38])[CH2:28][N:30]1[CH2:34][CH2:33][CH2:32][CH2:31]1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of (2-chloro-pyrimidin-4-yl)-quinolin-3-yl-amine (0.5 g, 1.8 mmol, 1.0 eq.) and 3-(4-amino-2-methoxy-phenyl)-1-pyrrolidin-1-yl-propan-1-one (0.47 g, 2.0 mmol, 1.1 eq. Step B) in 0.5 mL of DMSO was added a 1/1 (v/v) mixture of TFA/Et3N (337 μl, 1.8 mmol, 1.0 eq.). The reaction was heated to 100° C. and stirred for 16 h. The mixture was cooled, concentrated and purified by column chromatography (0-5% MeOH in CH2Cl2 with 1% of NH4OH (aq.)). Triturated with CH2Cl2 to provide the title compound. MS m/z=469.6 (M+H)+ Calc'd for C27H28N6O2: 468.56.

Workup

temperatureThe mixture was cooled
concentrationconcentrated
custompurified by column chromatography (0-5% MeOH in CH2Cl2 with 1% of NH4OH (aq.))
customTriturated with CH2Cl2

Sources & evidence

ORD record: ord-c686b7b979604241baf46f71522022e3
Source dataset: uspto-grants-2005_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06939874B2

Reaction notes

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