Diisopropylethylamine → HCID 86272147, compound

HRID 1505586Notes

Reaction equation

HRID 1505586 reaction equation
[NH2:1][C@H:2]([C:5]1[N:14]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:22]([F:25])([F:24])[F:23])[CH:16]=2)[C:13](=[O:26])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[F:27])[N:6]=1)[CH2:3][CH3:4].Cl[C:29]1[CH:34]=[CH:33][N:32]=[C:31]2[NH:35][CH:36]=[CH:37][C:30]=12.C(N(C(C)C)CC)(C)C>CC(O)(C)C>[NH:35]1[C:31]2=[N:32][CH:33]=[CH:34][C:29]([NH:1][C@H:2]([C:5]3[N:14]([C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([CH2:21][C:22]([F:25])([F:23])[F:24])[CH:16]=4)[C:13](=[O:26])[C:12]4[C:7](=[CH:8][CH:9]=[CH:10][C:11]=4[F:27])[N:6]=3)[CH2:3][CH3:4])=[C:30]2[CH:37]=[CH:36]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 117599585HCID 117599585, compound

Product 1

HCID 86272147HCID 86272147, 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-trifluoroethyl)phenyl)quinazolin-4(3H)-one (38 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 9A).

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-9976dedfda23415d8e46d545afcb90b5
Source dataset
uspto-grants-2015_12
Patent number
US09216985B2

Reaction notes

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