Diisopropylethylamine → HCID 16116973, compound

HRID 2355086Notes

Reaction equation

HRID 2355086 reaction equation
[F:1][C:2]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:16])=[C:11]([CH:15]=1)[C:12](O)=[O:13])=[O:5].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)C(C)C)C.[C:58]1([NH:64][C:65]2[N:70]=[CH:69][C:68]([NH2:71])=[CH:67][N:66]=2)[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1>CN(C=O)C.CO.CS(C)=O>[F:1][C:2]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:22])[F:23])=[CH:17][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]([CH3:16])=[C:11]([C:12]([NH:71][C:68]2[CH:67]=[N:66][C:65]([NH:64][C:58]3[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=3)=[N:70][CH:69]=2)=[O:13])[CH:15]=1)=[O:5]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 59381879HCID 59381879, compoundHCID 59381915HCID 59381915, compound

Product 1

HCID 16116973HCID 16116973, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 22036561Dimethyl sulfoxide methanolSolvent

Procedure

5-(2-fluoro-5-(trifluoromethyl)benzamido)-2-methylbenzoic acid 32 (0.25 g, 0.73 mmol), HATU (0.28 g, 0.73 mmol), and N-ethyl-N-isopropylpropan-2-amine (0.20 mL, 1.1 mmol) were taken up in DMF (6 mL). The solution was stirred at rt for 30 min then N2-phenylpyrimidine-2,5-diamine (0.105 g, 0.56 mmol) was added and the mixture was allowed to stir at rt overnight. The crude reaction mixture was taken up in minimal MeOH/DMSO and purified by preparative HPLC (acidic Gilson: 10-90% (0.1% TFA in CH3CN) in H2O over 15 min). Clean fractions were combined and allowed to stand for 2 h. Some product.TFA salt crashed out and was collected and neutralized with saturated NaHCO3 then extracted with CH2Cl2, dried over Na2SO4, filtered and concentrated to afford 2-fluoro-N-(4-methyl-3-(((2-(phenylamino)-5-pyrimidinyl)amino)carbonyl)phenyl)-5-(trifluoromethyl)benzamide 33 as a white solid. MS m/z found 510.1 [MH+]; calc. for C26H19F4N5O2=509.15.

Workup

  1. stirringto stir at rt overnight
  2. customThe crude reaction mixture
  3. custompurified by preparative HPLC (acidic Gilson: 10-90% (0.1% TFA in CH3CN) in H2O over 15 min)
  4. waitto stand for 2 h
  5. customwas collected
  6. extractionthen extracted with CH2Cl2
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1963a45f90184e6697d40c5e9f835747
Source dataset
uspto-grants-2010_07
Patent number
US07754717B2

Reaction notes

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