2-(Methylamino)ethanol → HCID 57731569, compound

HRID 2234691Notes

Reaction equation

HRID 2234691 reaction equation
[F:1][C:2]1[C:3]([NH:38][CH:39]2[CH2:44][CH2:43][CH:42]([OH:45])[CH2:41][CH2:40]2)=[C:4]([CH:8]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[CH:18][N:17](S(C4C=CC(C)=CC=4)(=O)=O)[C:14]3=[N:15][CH:16]=2)[CH:10]=1)[C:5](O)=[O:6].F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C.[CH3:79][NH:80][CH2:81][CH2:82][OH:83].[OH-].[K+]>C1COCC1.CS(C)=O.C(O)(=O)C>[F:1][C:2]1[C:3]([NH:38][CH:39]2[CH2:40][CH2:41][CH:42]([OH:45])[CH2:43][CH2:44]2)=[C:4]([CH:8]=[C:9]([C:11]2[CH:12]=[C:13]3[C:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=4[O:26][CH3:27])=[CH:18][NH:17][C:14]3=[N:15][CH:16]=2)[CH:10]=1)[C:5]([N:80]([CH2:81][CH2:82][OH:83])[CH3:79])=[O:6]

Participants

9

Reactant 5

HCID 80162-(Methylamino)ethanolHCID 14797Potassium HydroxideHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57731592HCID 57731592, compound

Product 1

HCID 57731569HCID 57731569, compoundYield 9%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-Fluoro-2-(4-hydroxy-cyclohexylamino)-5-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-benzoic acid (63 mg, 0.1 mmol) in anhydrous THF (1 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU) (57 mg, 0.15 mmol), diisopropylethylamine (52 μL, 0.3 mmol), and 2-methylaminoethanol (11 mg, 0.15 mmol). The reaction solution was irradiated in a Personal Chemistry Optimizer at 100° C. for 2 min and 200 μL of 50% w/v aqueous potassium hydroxide was added. The mixture was stirred for 15 h and 100 μL of glacial acetic acid was added. The suspension was dissolved in DMSO and water and directly purified by reverse-phase HPLC to afford the title compound as a white powder (5 mg, 0.009 mmol, 9% yield). 1H-NMR (500 MHz, d6-DMSO, 70° C.) δ=8.48 (d, J=2 Hz, 1H), 8.11 (d, J=2.0 Hz, 1H), 7.67 (s, 1H), 7.60 (dd, J=7 Hz, J2=2 Hz, 1H), 7.47 (dd, J1=14 Hz, J2=2.0 Hz, 1H), 7.28 (m, 1H), 7.22 (m, 1H), 7.12 (d, J=8.0 Hz, 1H), 7.05 (t, J=8.0 Hz, 1H), 4.55 (m, 1H), 3.99 (m, 1H), 3.82 (s, 3H), 3.11 (m, 1H), 2.97 (s, 3H), 2.9 (m, 3H), 2.76 (m, 2H), 2.66 (m, 2H), 1.92 (m, 4H), 1.56 (m, 4H); MS: m/z 533 [MH+].

Workup

  1. customThe reaction solution was irradiated in a Personal Chemistry Optimizer at 100° C. for 2 min
  2. additionwas added
  3. customwater and directly purified by reverse-phase HPLC

Sources & evidence

ORD record
ord-83c370fc7e26435a84c5a6f305d9ff6d
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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