Benzhydrylamine → HCID 86723959, compound
Reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]([CH2:20]O)([CH2:18]O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCN(C(C)C)C(C)C.FC(S(OS(C(F)(F)F)(=O)=O)(=O)=O)(F)F.[C:46]1([CH:52]([NH2:59])[C:53]2[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>C(Cl)Cl.C(#N)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([Cl:17])[CH:15]=2)[C:10]2([CH2:20][N:59]([CH:52]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:53]3[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=3)[CH2:18]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]Participants
Conditions
- Temperature
- 20 °C
Procedure
To a stirred mixture of 6-chloro-3,3-bis-hydroxymethyl-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester (0.31 g, 1 mmol), DIPEA (0.645 g, 5 mmol) and acetonitrile (5 mL) at −25° C. under nitrogen was added a solution of trifluoromethylsulfonic anhydride in DCM (1 M, 2.1 mL) dropwise over 0.3 h (T<−20° C.) and resulting mixture was stirred at −20° C. for 1 h), then a solution of C,C-diphenylmethylamine (0.179 g, 0.98 mmol) in acetonitrile (2 mL) was added (T<−20° C.) and stirring continued for 0.5 h. Mixture was warmed slowly to 20° C. and left thus for 16 h, heated at 75° C. for 8 h and then evaporated in vacuo. Chromatography (SiO2; gradient elution with 0-40% Et2O in petrol) gave the title compound (0.273 g). 1H NMR (CDCl3): 7.47 (4H, d), 7.35-7.27 (6H, m), 7.22 (2H, t), 7.05 (1H, dd), 4.41 (1H, s), 4.15-4.10 (2H, m), 3.37 (2H, d), 3.30 (2H, d), 1.64-1.55 (9H, m).
Workup
- customresulting mixture
- additionwas added (T<−20° C.)
- waitleft thus for 16 h
- temperatureheated at 75° C. for 8 h
- customevaporated in vacuo
- washChromatography (SiO2; gradient elution with 0-40% Et2O in petrol)
Sources & evidence
- ORD record
- ord-7d77d8d6839f493d9e12ad6651e81514
- Source dataset
- uspto-grants-2015_04
- Patent number
- US09018214B2
Reaction notes
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