Dimethylamine → HCID 59825046, compound

HRID 886561Notes

Reaction equation

HRID 886561 reaction equation
[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])=[CH:19][N:18](S(C4C=CC(C)=CC=4)(=O)=O)[C:15]3=[N:16][CH:17]=2)[N:7]=1)[C:3]([OH:5])=O.[CH3:39][NH:40][CH3:41].C(N(C(C)C)CC)(C)C.[OH-].[Na+]>O1CCCC1.C(O)(=O)C.CO>[OH:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]2[CH:13]=[C:14]3[C:20]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[O:27][CH3:28])=[CH:19][NH:18][C:15]3=[N:16][CH:17]=2)[N:7]=1)[C:3]([N:40]([CH3:41])[CH3:39])=[O:5]

Participants

8

Reactant 4

HCID 674DimethylamineHCID 14798Sodium HydroxideHCID 81531DiisopropylethylamineHCID 59824974HCID 59824974, compound

Product 1

HCID 59825046HCID 59825046, compoundYield 16.3%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a microwave vial O-(7-azabenzotriazol-1-yl)-N,N,N′N′-tetramethyluronium hexafluorophosphate 53.9 mg, 0.14 mmol) was added to a solution of hydroxy-{6-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-acetic acid (75 mg, 0.14 mmol), dimethyl amine (2 M solution in THF, 65 μl, 0.14 mmol) and di-iso-propyl ethyl amine (75 μl, 0.43 mmol) in tetrahydrofuran (1 ml). The vial was sealed and the solution irradiated to 70° C. for 10 min in a microwave reactor. Methanol (2 ml) was then added to the solution followed by 50% w/v aqueous sodium hydroxide (200 μl) and stirred at room temperature for 2 hours. The reaction was then neutralized with acetic acid and purified by preparative high pressure liquid chromatography, to give 2-hydroxy-2-{6-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-pyridin-2-yl}-N,N-dimethyl-acetamide (9.2 mg, 16% yield). 1H NMR (500 MHz, Dimethyl sulfoxide-d6) δ 2.86 (s, 3H) 3.32 (s, 3H); 3.82 (s, 3H)); 5.61 (m, 2H); 7.06 (t, J=8 Hz 1H); 7.15 (d, J=8 Hz, 1H) 7.31 (t, J=8 Hz, 1H); 7.44 (d, J=7.5 Hz 1H); 7.58 (d, J=8 Hz 1H); 7.73 (s, 1H); 7.58 (t, J=7.5 Hz 1H); 7.95 (d, J=7.5 Hz 1H); 7.94 (s, 1H); 8.60 (s, 1H); 8.95 (s, 1H); 11.98 (s, br, 1H) MS: m/z 403.4 (M+H+).

Workup

  1. customThe vial was sealed
  2. customthe solution irradiated to 70° C. for 10 min in a microwave reactor
  3. custompurified by preparative high pressure liquid chromatography

Sources & evidence

ORD record
ord-1a353f0913114a5881c84f0af404a283
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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