Trifluoroacetic acid methylene chloride → HCID 117728680, compound

HRID 718632Notes

Reaction equation

HRID 718632 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([CH:28]4[CH2:33][CH2:32][N:31]([CH2:34][C:35]([O:37]C(C)(C)C)=[O:36])[CH2:30][CH2:29]4)=[C:14]([C:16]#[C:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1.[C:42]([OH:48])([C:44]([F:47])([F:46])[F:45])=[O:43].C(Cl)Cl>>[F:45][C:44]([F:47])([F:46])[C:42]([OH:48])=[O:43].[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[N:9]([C:13]([CH:28]4[CH2:33][CH2:32][N:31]([CH2:34][C:35]([OH:37])=[O:36])[CH2:30][CH2:29]4)=[C:14]([C:16]#[C:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)[N:15]=3)[N:10]=[CH:11][CH:12]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 117732497HCID 117732497, compound

Product 1

HCID 117728680HCID 117728680, compound

Procedure

A solution of compound 41g (0.20 g, 0.36 mmol) in TFA/CH2Cl2 (1:3, 3 mL) was stirred at rt for 2 h, and concentrated under reduced pressure. The resulting mixture was diluted with 10 mL of water. The solids formed were collected by filtration and washed with Et2O (2×30 mL). The crude solid product was then purified by re-crystallization from CH2Cl2:Et2O (1:10) to obtain the title compound 25 as a yellow solid. 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 8.48 (d, J=8.4 Hz, 1H), 8.24 (d, J=5.7 Hz, 1H), 8.06-8.03 (m, 2H), 7.87-7.80 (m, 2H), 7.70-7.65 (m, 1H), 6.41 (d, J=6.0 Hz, 1H), 4.19 (s, 2H), 4.08-3.95 (m, 4H), 3.82-3.64 (m, 7H), 3.42-3.29 (m, 2H), 2.70-2.57 (m, 2H), 2.23-2.19 (m, 2H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H28N6O3: 497.2 (M+H). Found: 497.2.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe resulting mixture was diluted with 10 mL of water
  3. customThe solids formed
  4. filtrationwere collected by filtration
  5. washwashed with Et2O (2×30 mL)
  6. customThe crude solid product was then purified by re-crystallization from CH2Cl2:Et2O (1:10)

Sources & evidence

ORD record
ord-f635573a6b784ba18a548d0104b57f94
Source dataset
uspto-grants-2015_11
Patent number
US09193736B2

Reaction notes

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