Benzylamine → HCID 67045241, compound

HRID 2367095Notes

Reaction equation

HRID 2367095 reaction equation
[CH3:1][Si:2]([CH3:28])([CH3:27])[CH2:3][CH2:4][O:5][CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([C:16]([C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20]([OH:22])=O)=[O:17])=[CH:13][CH:14]=2)[CH:9]=[CH:8]1.CN1CCOCC1.C1C=NC2N(O)N=NC=2C=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH2:70]([NH2:77])[C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1>CN(C)C=O.C(=O)(O)[O-].[Na+].C(OCC)(=O)C>[OH:17][C:16]1([C:12]2[CH:11]=[C:10]3[C:15](=[CH:14][CH:13]=2)[N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:27])([CH3:1])[CH3:28])[CH:8]=[CH:9]3)[C:18]2[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:20](=[O:22])[N:77]1[CH2:70][C:71]1[CH:76]=[CH:75][CH:74]=[CH:73][CH:72]=1

Participants

9

Reactant 5

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 181649HOAtHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 67044512HCID 67044512, compound

Product 1

HCID 67045241HCID 67045241, compoundYield 58%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
60 °C

Procedure

Crude 2-{[1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indol-5-yl]carbonyl}benzoic acid (0.32 mmol) was taken up in N,N-dimethylformamide (1.0 mL), and treated with 4-methylmorpholine (0.14 mL, 1.3 mmol), HOAt (0.065 g, 0.48 mmol), HATU (0.16 g, 0.42 mmol) and benzylamine (0.070 mL, 0.64 mmol) and heated for 12 h at 60° C. The solution was diluted with saturated aqueous sodium bicarbonate solution and ethyl acetate and the layers were separated. The aqueous layer was extracted (2×100 mL ethyl acetate) and the combined organic layers were dried (sodium sulfate), filtered and concentrated in vacuo. Column chromatography (silica gel, 3:1 hexanes/ethyl acetate) gave 0.089 g (58%) of 3-hydroxy-2-(phenylmethyl)-3-[1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-indol-5-yl]-2,3-dihydro-1H-isoindol-1-one. 1H NMR (400 MHz, d6-CDCl3): 8.10 (d, 1H), 7.97 (m, 2H), 7.69 (m, 3H), 7.56 (m, 5H), 7.42 (m, 4H), 7.34 (m, 1H), 5.49 (m, 2H), 3.51 (m, 2H), 0.95 (m, 2H), 0.00 (s, 9H).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted (2×100 mL ethyl acetate)
  3. dry with materialthe combined organic layers were dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b17ea69ec4854878a7a34bf91ba3fa7d
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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