Trifluoroacetic acid methylene chloride → HCID 117728225, compound

HRID 1772615Notes

Reaction equation

HRID 1772615 reaction equation
C([CH:5]([N:9](C(OC(C)(C)C)=O)[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]3[CH:22]=[C:23](/[CH:25]=[CH:26]/[C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)[N:24]=[C:20]3[C:19]([N:37]3[CH2:42][CH2:41][O:40][CH2:39][CH2:38]3)=[N:18][CH:17]=2)=[CH:12][N:11]=1)[C:6]([O-:8])=[O:7])(C)(C)C.C(Cl)Cl.[C:53]([OH:59])([C:55]([F:58])([F:57])[F:56])=[O:54]>>[F:56][C:55]([F:58])([F:57])[C:53]([OH:59])=[O:54].[O:40]1[CH2:39][CH2:38][N:37]([C:19]2[C:20]3[N:21]([CH:22]=[C:23](/[CH:25]=[CH:26]/[C:27]4[CH:36]=[CH:35][C:34]5[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=5)[N:28]=4)[N:24]=3)[C:16]([C:13]3[CH:14]=[CH:15][C:10]([NH:9][CH2:5][C:6]([OH:8])=[O:7])=[N:11][CH:12]=3)=[CH:17][N:18]=2)[CH2:42][CH2:41]1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 131734670HCID 131734670, compound

Product 1

HCID 117728225HCID 117728225, compoundYield 25%

Procedure

A solution of compound 13b (200 mg, 0.300 mmol) in DCM/TFA (4:1 v/v, 10 mL) was stirred at rt for 30 min. Solvent was evaporated, and water (5 mL) was added. The resulting solids were collected by filtration and washed with Et2O to obtain the title compound as a yellow solid (40.2 mg, 25% yield). 1H-NMR (300 MHz, DMSO-d6) δ (ppm): 8.44 (d, J=8.7 Hz, 1H), 8.29-8.23 (m, 1H), 8.18 (s, 1H), 8.03-7.91 (m, 4H), 7.85-7.73 (m, 2H), 7.71 (s, 1H), 7.65-7.52 (m, 2H), 7.51-7.40 (m, 1H), 7.38 (s, 1H), 6.85 (d, J=8.4 Hz, 1H), 4.40-4.20 (m, 4H), 4.18-4.01 (m, 2H), 3.93-3.77 (m, 4H). Mass Spectrum (LCMS, ESI pos.): Calcd. for C28H25N7O3: 508.2 (M+H). Found 508.3.

Workup

  1. customSolvent was evaporated
  2. additionwater (5 mL) was added
  3. filtrationThe resulting solids were collected by filtration
  4. washwashed with Et2O

Sources & evidence

ORD record
ord-ab52180c71dd4a6396b38e0cb77b3fa7
Source dataset
uspto-grants-2016_02
Patent number
US09249163B2

Reaction notes

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