Diisopropylethylamine → HCID 178515150, compound

HRID 1505579Notes

Reaction equation

HRID 1505579 reaction equation
[NH2:1][C@H:2]([C:8]1[N:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:16](=[O:24])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[F:25])[N:9]=1)[CH2:3][C:4]([F:7])([F:6])[F:5].Br[C:27]1[N:35]=[CH:34][N:33]=[C:32]2[C:28]=1[N:29]=[CH:30][NH:31]2.C(N(C(C)C)CC)(C)C>CC(O)(C)C>[N:35]1[C:27]([NH:1][C@H:2]([C:8]2[N:17]([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:16](=[O:24])[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][C:14]=3[F:25])[N:9]=2)[CH2:3][C:4]([F:6])([F:5])[F:7])=[C:28]2[C:32]([NH:31][CH:30]=[N:29]2)=[N:33][CH:34]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 117599857HCID 117599857, compoundHCID 178419477HCID 178419477, compound

Product 1

HCID 178515150HCID 178515150, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Conditions

Temperature
80 °C

Procedure

Under nitrogen, to (S)-2-(1-amino-3,3,3-trifluoropropyl)-5-fluoro-3-phenylquinazolin-4(3H)-one (5) (35 mg, 0.10 mmol, 1.0 equiv) in t-BuOH (0.5 mL) at 23° C. was added 6-bromo-9H-purine (6) (30 mg, 0.15 mmol, 1.5 equiv) and diisopropylethylamine (35 μL, 0.20 mmol, 2.0 equiv). After stirring for 3 days at 80° C. in a sealed tube, the reaction mixture was concentrated in vacuo and the residue was purified by preparative TLC eluting with CH2Cl2/MeOH to afford 10 mg of compound 2A as a colorless solid (21%).

Workup

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

Sources & evidence

ORD record
ord-4bfe4f3796974d70a4175c93dc88656e
Source dataset
uspto-grants-2015_12
Patent number
US09216985B2

Reaction notes

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