Diisopropylethylamine → (S)-2-(1-((1H-pyrrolo[2,3-b]pyridin-4-yl)amino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one

HRID 1505581Notes

Reaction equation

[NH2:1][C@H:2]([C:5]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:13](=[O:21])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[F:22])[N:6]=1)[CH2:3][CH3:4].Cl[C:24]1[CH:29]=[CH:28][N:27]=[C:26]2[NH:30][CH:31]=[CH:32][C:25]=12.C(N(C(C)C)CC)(C)C>CC(O)(C)C>[NH:30]1[C:26]2=[N:27][CH:28]=[CH:29][C:24]([NH:1][C@H:2]([C:5]3[N:14]([C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[C:13](=[O:21])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][C:11]=4[F:22])[N:6]=3)[CH2:3][CH3:4])=[C:25]2[CH:32]=[CH:31]1

Participants

Conditions

Temperature: 120 °C

Procedure

Under nitrogen, to (S)-2-(1-aminopropyl)-5-fluoro-3-phenylquinazolin-4(3H)-one (27 mg, 0.091 mmol, 1.0 equiv) in t-BuOH (0.5 mL) at 23° C. is added 4-chloro-1H-pyrrolo[2,3-b]pyridine (21 mg, 0.14 mmol, 1.5 equiv) and diisopropylethylamine (63 μL, 0.36 mmol, 4.0 equiv). After stirring for 48 hr at 120° C. in a sealed tube, the reaction mixture is concentrated in vacuo and the residue is purified by preparative TLC eluting with CH2Cl2/MeOH to afford the title compound (Compound 5A).

Workup

concentrationthe reaction mixture is concentrated in vacuo
customthe residue is purified by preparative TLC
washeluting with CH2Cl2/MeOH

Sources & evidence

ORD record: ord-5a53e848214b4b2f901fffbc86dd7520
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216985B2

Reaction notes

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