Diethyl Ether → HCID 11178018, compound

HRID 1678206Notes

Reaction equation

HRID 1678206 reaction equation
C(OC([N:8]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]2[N:23]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[C:16]=2[CH:30]=[O:31])[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(#N)C.CCOCC>ClCCl>[N:11]1([C:15]2[N:23]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:18]3=[N:19][CH:20]=[CH:21][CH:22]=[C:17]3[C:16]=2[CH:30]=[O:31])[CH2:12][CH2:13][CH2:14][NH:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6342AcetonitrileHCID 6422Trifluoroacetic acid2×HCID 86596816HCID 86596816, compound

Product 1

HCID 11178018HCID 11178018, compoundYield 113.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-(3-formyl-1-phenyl-1H-pyrrolo[2,3-b]pyridin-2-yl)-[1,4]diazepane-1-carboxylic acid tert-butyl ester (330 mg, 0.786 mmol) in dichloromethane (20 mL) is treated with trifluoroacetic acid (0.60 mL, 6.04 mmol). The resulting solution is allowed to stir at room temperature for 22 hours before treating the reaction with a further aliquot of trifluoroacetic acid (0.60 mL, 6.04 mmol). After stirring for a further 18 hours, the reaction mixture is evaporated to give a gooey red oil. Trituration of the crude product salt with acetonitrile and ether gives 285 mg of 2-[1,4]diazepan-1-yl-1-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde; trifluoro-acetic acid salt as a pink solid (84% yield). LC/MS: retention time 2.25 min, m/e 321 (M+H). 1H NMR (300 MHz, DMSO-d6): 10.15 (1H, s), 8.60 (2H, br.s), 8.36 (1H, dd), 8.08 (1H, dd), 7.63-7.48 (5H, m), 7.22 (1H, dd), 3.63-3.48 (4H, m), 3.11-2.95 (4H, m), 1.81 (2H, m).

Workup

  1. additionbefore treating
  2. stirringAfter stirring for a further 18 hours
  3. customthe reaction mixture is evaporated
  4. customto give a gooey red oil

Sources & evidence

ORD record
ord-2f9bc513de32444f91c4a393be8bd7ac
Source dataset
uspto-grants-2011_08
Patent number
US08008491B2

Reaction notes

Loading…