Acetic Acid → HCID 57731483, compound

HRID 2234689Notes

Reaction equation

HRID 2234689 reaction equation
F[C:2]1[C:12]([F:13])=[CH:11][C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[CH:21][N:20](S(C4C=CC(C)=CC=4)(=O)=O)[C:17]3=[N:18][CH:19]=2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].[CH3:41][N:42]1[CH2:47][CH2:46][CH:45]([NH2:48])[CH2:44][CH2:43]1.[OH-].[K+].C(O)(=O)C>CO.CC(C)=O>[F:13][C:12]1[C:2]([NH:48][CH:45]2[CH2:46][CH2:47][N:42]([CH3:41])[CH2:43][CH2:44]2)=[C:3]([CH:9]=[C:10]([C:14]2[CH:15]=[C:16]3[C:22]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[O:29][CH3:30])=[CH:21][NH:20][C:17]3=[N:18][CH:19]=2)[CH:11]=1)[C:4]([N:6]([CH3:7])[CH3:8])=[O:5]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 27375314-Amino-1-methylpiperidineHCID 57731625HCID 57731625, compound

Product 1

HCID 57731483HCID 57731483, compoundYield 4.5%

Reagents, catalysts & solvents 1

HCID 21894497Aceton-methanolSolvent

Procedure

Into a 5 mL screw-cap vial were added 2,3-Difluoro-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-N,N-dimethyl-benzamide (100 mg, 0.178 mmol) and 1-methyl-piperidin-4-ylamine (102 mg, 0.712 mmol). The vial was sealed and placed in heated block at 120° C. for 48 h. The reaction solution was dissolved in 1:1 methanol/acetone (2 mL total) and treated with 100 μL of 50% w/w aqueous potassium hydroxide for 1 h. Glacial Acetic acid was added to obtain pH 7, then the reaction mixture was concentrated. The residue was purified by reverse-phase HPLC to afford the title compound as a white powder (4 mg, 0.008 mmol, 4% yield). 1H-NMR (500 MHz, d6-DMSO) δ=11.87 (d, J=2 Hz, 1H), 8.49 (d, J=2.5 Hz, 1H), 8.12 (d, J=2.0 Hz, 1H), 7.71 (d, J=2.5 Hz, 1H), 7.61 (dd, J1=8.0 Hz, J2=2.0 Hz, 1H), 7.54 (dd, J=13.5 Hz, J2=2.0 Hz, 1H), 7.24-7.3 (m, 2H), 7.12 (dd, J1=8.5 Hz, J2=1.0 Hz, 1H), 7.04 (td, J1=7.5 Hz, J2=1.0 Hz, 1H), 4.57 (dd, J1=5 Hz, J2=2.5 Hz, 1H), 3.81 (s, 3H), 3.14 (m, 1H), 3.00 (s, 3H), 2.9 (s, 3H), 3.14 (m, 1H), 2.12 (s, 3H), 1.87 (m, 2H), 1.74 (m, 2H), 1.41 (m, 2H); MS: m/z 502 [MH+].

Workup

  1. customInto a 5 mL screw-cap vial
  2. customThe vial was sealed
  3. customto obtain pH 7
  4. concentrationthe reaction mixture was concentrated
  5. customThe residue was purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-c0c38f6e01c54c18a6af819b4226f93b
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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