Trifluoroacetic acid → HCID 22396828, compound

HRID 1370440Notes

Reaction equation

HRID 1370440 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[C:17]2[N:16]([CH2:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH2:27][CH2:28][N:29](C(OC(C)(C)C)=O)[CH2:30][CH2:31][C:14]=3[C:13]=2[C:12]([Cl:39])=[CH:11][CH:10]=1.[OH-].[Na+]>C(Cl)Cl>[ClH:8].[Cl:8][C:9]1[C:17]2[N:16]([CH2:18][CH2:19][O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH2:27][CH2:28][NH:29][CH2:30][CH2:31][C:14]=3[C:13]=2[C:12]([Cl:39])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 22396561HCID 22396561, compound

Product 1

HCID 22396828HCID 22396828, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.65 mL, 8.4 mmol) was added to a solution of tert-butyl 7,10-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 51 mg (30%) of a white solid: mp 261.0-263.0° C.; 1H NMR (300 MHz, DMSO) δ 9.24 (br s, 2H), 7.26 (m, 2H), 7.16 (d, J=8.3 Hz, 1H), 7.06 (d, J=8.3 Hz, 1H), 6.90 (m, 3H), 4.97 (t, J=4.9 Hz, 2H), 4.26 (m, 2H), 3.53 (m, 2H); 13C NMR (300 MHz, DMSO) δ 157.8, 141.3, 131.1, 129.4, 125.5, 123.4, 123.2, 121.3, 120.8, 114.4, 114.1, 111.4, 67.7, 44.8, 43.2, 43.1, 22.2, 20.9; IR (diffuse reflectance) 2965, 2952, 2826, 2794, 2741, 2676, 2650, 2443, 1496, 1467, 1241, 1234, 1170, 804, 755 cm−1; MS (EI) m/z 374 (M+), 339, 334, 332, 84, 78, 77, 65, 63, 61; Anal. Calcd for C20H20Cl2N2O.HCl: C, 58.34; H, 5.14; N, 6.80; found: C, 58.25; H, 5.23; N, 6.80.

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-aa0c713a36fb421f82d96b02f4369361
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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