Reaction equation
[NH2:1][CH:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][C:13]#[N:14])=[CH:9][CH:10]=2)[O:5][CH2:4][CH2:3]1.[C:15]1([CH:21]([NH:26][S:27]([C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:38])[F:37])[CH:31]=2)(=[O:29])=[O:28])[CH2:22][C:23](O)=[O:24])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(Cl)CCl.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:13]([CH2:12][C:8]1[CH:7]=[C:6]2[C:11]([CH:2]([NH:1][C:23](=[O:24])[CH2:22][CH:21]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:26][S:27]([C:30]3[CH:35]=[CH:34][CH:33]=[C:32]([C:36]([F:39])([F:37])[F:38])[CH:31]=3)(=[O:29])=[O:28])[CH2:3][CH2:4][O:5]2)=[CH:10][CH:9]=1)#[N:14]Participants
7
Reactant 5
HCID 111,2-Dichloroethane
HCID 81531Diisopropylethylamine
HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)
HCID 454390913-Phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionic acid
HCID 68929026(4-Amino-chroman-7-yl)-acetonitrileProduct 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (4-amino-chroman-7-yl)-acetonitrile (Step A, 400 mg, 2.15 mmol) in CH2Cl2 (15 mL) was added 3-phenyl-3-(3-trifluoromethyl-benzenesulfonylamino)-propionic acid (802 mg, 2.15 mmol), HATU (408 mg, 1.07 mmol), EDC (453 mg, 2.36 mmol), and DIEA (0.7 mL, 4.29 mmol). The resulting mixture was stirred at RT for 18 h. Solvent was evaporated in vacuo. The residue was purified by chromatography on silica gel. Elution with CH2Cl2:MeOH mixture (95:5) gave final compound. MS m/z: 544.12 (M+H). Calc'd. for C27H24F3N3O4S-543.56.
Workup
- customSolvent was evaporated in vacuo
- customThe residue was purified by chromatography on silica gel
- washElution with CH2Cl2
Sources & evidence
- ORD record
- ord-fbff2b1639764c1eba5441021395fb1d
- Source dataset
- uspto-grants-2008_09
- Patent number
- US07425631B2
Linked notes
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