Potassium Carbonate → HCID 56970956, compound

HRID 919624Notes

Reaction equation

HRID 919624 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:22][CH:21]([NH:23][C:24]3[C:25]4[CH:32]=[CH:31][N:30](S(C5C=CC(C)=CC=5)(=O)=O)[C:26]=4[N:27]=[CH:28][N:29]=3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C([O-])([O-])=O.[K+].[K+]>CO.O>[Cl:8][C:6]1[CH:5]=[C:4]([NH:9][CH2:10][C:11]([N:13]2[CH2:22][CH:21]([NH:23][C:24]3[C:25]4[CH:32]=[CH:31][NH:30][C:26]=4[N:27]=[CH:28][N:29]=3)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])[CH:3]=[C:2]([Cl:1])[CH:7]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86706480HCID 86706480, compound

Product 1

HCID 56970956HCID 56970956, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-(3,5-dichlorophenylamino)-1-(4-(7-tosyl-7H-pyrrolo[2,3-d]pyrimidin-4-ylamino)-3,4-dihydroisoquinolin-2(1H)-yl)ethanone (0.15 g, 0.24 mmol) in MeOH (4 mL) and water (1 mL) was added K2CO3 (0.133 g, 0.96 mmol) and heated to 60° C. for 2 h. The reaction mixture was concentrated in vacuo to give a residue that was purified by column chromatography (silica gel, gradient MeOH in DCM) to give (25 mg, 23%) of the titled compound. 1H NMR (DMSO-d6, 400 MHz): δ 11.75 (s, 1H), 8.52 (s, 1H), 8.18 (s, 1H), 7.68-7.62 (m, 1H), 7.42-7.18 (4H, m), 6.71-6.56 (m, 3H), 5.19 (s, 1H), 5.06 (s, 1H), 4.23 (d, J=12 Hz, 1H) 4.12-3.94 (bs, 1H), 3.82-3.65 (m, 1H), 2.75 (m, 2H)

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto give a residue that
  3. customwas purified by column chromatography (silica gel, gradient MeOH in DCM)

Sources & evidence

ORD record
ord-b1619e2439ec4cdd9c250922e6789595
Source dataset
uspto-grants-2016_03
Patent number
US09273028B2

Reaction notes

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