Diisopropylethylamine → HCID 86272623, compound

HRID 1505589Notes

Reaction equation

HRID 1505589 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]=[CH:38][C:31]=12.C(N(C(C)C)CC)(C)C>CC(O)(C)C>[NH:36]1[C:32]2=[N:33][CH:34]=[CH:35][C:30]([NH:1][C@H:2]([C:5]3[N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH2:22][C:23]([F:26])([F:24])[F:25])[CH:16]=4)[C:13](=[O:27])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][C:11]=4[F:28])[N:6]=3)[CH2:3][CH3:4])=[C:31]2[CH:38]=[CH:37]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 117599614HCID 117599614, compound

Product 1

HCID 86272623HCID 86272623, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

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 4-chloro-1H-pyrrolo[2,3-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 13A).

Workup

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

Sources & evidence

ORD record
ord-b57c3fdb84cd475890be514a1c26c0b6
Source dataset
uspto-grants-2015_12
Patent number
US09216985B2

Reaction notes

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