Diisopropylethylamine → HCID 178456060, compound

HRID 1505588Notes

Reaction equation

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

Participants

Conditions

Temperature: 120 °C

Procedure

Under nitrogen, to (S)-2-(1-aminopropyl)-5-fluoro-3-(3-(2,2,2-trifluoroethoxy)phenyl)quinazolin-4(3H)-one (40 mg, 0.10 mmol, 1.0 equiv) in t-BuOH (0.5 mL) at 23° C. is added 7-chloro-3H-imidazo[4,5-b]pyridine (23 mg, 0.15 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 12A).

Workup

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

Sources & evidence

ORD record: ord-bd22e3fbe03641af8952a95684707337
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09216985B2

Reaction notes

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