Dichloromethane → HCID 59362523, compound

HRID 1625459Notes

Reaction equation

HRID 1625459 reaction equation
C([O:5][C:6](=[O:53])[CH2:7][O:8][C:9]1[CH:14]=[C:13]([CH2:15][NH:16][C:17]([C:19]2[C:20](=[O:34])[N:21]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[C:28]([F:33])[CH:27]=3)[CH:22]=[CH:23][CH:24]=2)=[O:18])[CH:12]=[C:11]([C:35]2[C:43]3[C:38](=[N:39][CH:40]=[CH:41][CH:42]=3)[N:37](S(C3C=CC=CC=3)(=O)=O)[CH:36]=2)[CH:10]=1)(C)(C)C.FC(F)(F)C(O)=O.C(Cl)Cl>>[F:33][C:28]1[CH:27]=[C:26]([CH:31]=[CH:30][C:29]=1[F:32])[CH2:25][N:21]1[CH:22]=[CH:23][CH:24]=[C:19]([C:17]([NH:16][CH2:15][C:13]2[CH:14]=[C:9]([CH:10]=[C:11]([C:35]3[C:43]4[C:38](=[N:39][CH:40]=[CH:41][CH:42]=4)[NH:37][CH:36]=3)[CH:12]=2)[O:8][CH2:7][C:6]([OH:53])=[O:5])=[O:18])[C:20]1=[O:34]

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 59362432HCID 59362432, compound

Product 1

HCID 59362523HCID 59362523, compoundYield 40%

Procedure

A mix of [3-(1-Benzenesulfonyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-({[1-(3,4-difluoro-benzyl)-2-oxo-1,2-dihydro-pyridine-3-carbonyl]-amino}-methyl)-phenoxy]-acetic acid tert-butyl ester (20 mg, 0.00003 mol) and Trifluoroacetic Acid (20 mg, 0.0001 mol;) in Methylene chloride (8 mL, 0.1 mol) was stirred for overnight. LC-MS showed only formation of the des-phSO2 and saponified product C (1.24 min, ES+/545.64). Evaporated off the solvents and dissolved in DMSO and water and purified on Gilson HPLC to give the desired product (6 mg, 40%) MS (ES+) m/z 545.64 (M+1). 1H NMR (DMSO, 400 MHz): δ 8.41 (dd, 1H), 8.26 (d, 2H), 8.24 (dd, 1H), 7.88 (s, 2H), 7.45-7.35 (m, 2H), 7.30 (s, 2H), 7.18 (m, 1H), 7.10-7.07 (m, 2H), 6.77 (s, 2H), 6.60 (t, 1H), 5.22 (s, 2H), 4.75 (s, 2H), 4.55 (d, 2H),

Workup

  1. customEvaporated off the solvents
  2. dissolutiondissolved in DMSO
  3. customwater and purified on Gilson HPLC

Sources & evidence

ORD record
ord-68b8383d81ac4191b7e75fc248956cb1
Source dataset
uspto-grants-2014_07
Patent number
US08778977B2

Reaction notes

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