Trifluoroacetic acid → HCID 69896702, compound

HRID 1356390Notes

Reaction equation

HRID 1356390 reaction equation
C(O)(C(F)(F)F)=O.[Cl:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]([CH2:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=3[CH3:29])=[O:20])[C@H:13]3[CH2:30][CH2:31][N:32](C(OC(C)(C)C)=O)[CH2:33][CH2:34][C@H:12]3[C:11]=2[C:10]=1[Cl:42]>C(Cl)Cl>[ClH:8].[Cl:8][C:9]1[CH:17]=[CH:16][C:15]2[N:14]([CH2:18][C:19]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:23]=3[CH3:29])=[O:20])[C@H:13]3[CH2:30][CH2:31][NH:32][CH2:33][CH2:34][C@H:12]3[C:11]=2[C:10]=1[Cl:42]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86585360HCID 86585360, compound

Product 1

HCID 69896702HCID 69896702, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (0.60 mL, 7.7 mmol) was added to a solution of tert-butyl (5aS*,10bS*)-9,10-dichloro-6-{ 2-[(2,3-dimethylphenyl)amino]-2-oxoethyl } -1,4,5,5a,6,10b-hexahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.20 g, 0.39 mmol) in CH2Cl2 (7 mL). The reaction was quenched with 10% aqueous NaOH (5 mL) after 2.5 h and extracted with CH2Cl2 (3×25 mL). The combined organic layers were washed with brine, dried over Na2SO4, decanted, and concentrated. The crude yellow foam (0.15 g) was purified via column chromatography (Biotage, 40S) with CH2Cl2/MeOH/NH4OH (976:21:3) followed by the preparation of the hydrochloride salt to give 67 mg (38%) of an off white solid: mp 238.5-241.0° C.; 1H NMR (DMSO, 300 MHz) δ 9.60 (s, 1H), 8.92 (br s, 2H), 7.30 (d, J=8.4 Hz, 1H), 7.13 (m, 1H), 7.03 (m, 2H), 6.54 (d, J=8.7 Hz, 1H), 4.24 (m, 1H), 4.16 (d, J=17.1 Hz, 1H), 3.87 (d, J=17.1 Hz, 1H), 3.71 (m, 1H), 3.35 (m, 2H), 3.08 (m, 3H), 2.34 (m, 1H), 2.24 (m, 3H), 2.12 (m, 5H); IR (diffuse reflectance) 2969, 2955, 2938, 2823, 2796, 2772, 2755, 2727, 1676, 1527, 1464, 1285, 1274, 806, 787 cm−1; MS (EI) m/z 417 (M+), 419, 226, 120, 106, 105, 91, 77, 76, 56; HRMS (FAB) calcd for C22H25CL2N3O+H 418.1453, found 418.1439.

Workup

  1. customThe reaction was quenched with 10% aqueous NaOH (5 mL) after 2.5 h
  2. extractionextracted with CH2Cl2 (3×25 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over Na2SO4
  5. customdecanted
  6. concentrationconcentrated
  7. customThe crude yellow foam (0.15 g) was purified via column chromatography (Biotage, 40S) with CH2Cl2/MeOH/NH4OH (976:21:3)
  8. customfollowed by the preparation of the hydrochloride salt
  9. customto give 67 mg (38%) of an off white solid

Sources & evidence

ORD record
ord-5e9cc8ca3861430eb768405bf0aa14f8
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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