Trifluoroacetic acid → HCID 22396893, compound

HRID 2307008Notes

Reaction equation

HRID 2307008 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:10]=[C:11]([Cl:39])[C:12]2[C:13]3[CH2:31][CH2:30][N:29](C(OC(C)(C)C)=O)[CH2:28][CH2:27][C:14]=3[N:15]([CH2:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16]=2[CH:17]=1.[OH-].[Na+]>C(Cl)Cl>[ClH:8].[Cl:8][C:9]1[CH:10]=[C:11]([Cl:39])[C:12]2[C:13]3[CH2:31][CH2:30][NH:29][CH2:28][CH2:27][C:14]=3[N:15]([CH2:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:16]=2[CH:17]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 22396719HCID 22396719, compound

Product 1

HCID 22396893HCID 22396893, compoundYield 65.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.65 mL, 8.4 mmol) was added to a solution of tert-butyl 8,10-dichloro-6-(2-phenoxyethyl)-1,4,5,6-tetrahydroazepino[4,5-b]indole-3 (2H)-carboxylate (0.20 g, 0.42 mmol) in CH2Cl2 (6 mL). After 5 h, the reaction was made basic with 10% aqueous NaOH and extracted with CH2Cl2 (3×15 mL). The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated to give a crude solid. After the hydrochloride salt was prepared, it was further purified by recrystallization from MeOH/EtOAc to give 57 mg (33%) of a white solid: mp 242.0-243.0° C.; 1H NMR (300 MHz, DMSO) δ 9.13 (br s, 2H), 7.72 (d, J=1.7 Hz, 1H), 7.26 (m, 2H), 7.13 (d, J=1.7 Hz, 1H), 6.92 (t, J=7.4 Hz, 1H), 6.84 (d, J=7.9 Hz, 2H), 4.64 (m, 2H), 4.17 (m, 2H), 3.49 (m, 2H); 13C NMR (300 MHz, DMSO) δ 157.7, 139.8, 136.7, 129.4, 125.2, 124.4, 121.5, 120.8, 120.0, 114.1, 110.4, 109.6, 66.5, 45.2, 43.6, 42.3, 22.3, 21.0; IR (diffuse reflectance) 2843, 2718, 2688, 2666, 2633, 2440, 1601, 1497, 1460, 1244, 1238, 845, 827, 754, 694 cm 1; MS (EI) m/z 376, 374 (M+), 339, 334, 333, 332, 78, 77, 65, 63; Anal. Calcd for C20H20Cl2N2O.HCl: C, 58.34; H, 5.14; N, 6.80; found: C, 58.10; H, 5.20; N, 6.76.

Workup

  1. extractionextracted with CH2Cl2 (3×15 mL)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customdecanted
  5. concentrationconcentrated
  6. customto give a crude solid
  7. customit was further purified by recrystallization from MeOH/EtOAc

Sources & evidence

ORD record
ord-377340493c7343bcbe2f12627bd70811
Source dataset
uspto-grants-2004_12
Patent number
US06828314B2

Reaction notes

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