Dimethylamine → HCID 59825095, compound

HRID 886562Notes

Reaction equation

HRID 886562 reaction equation
C(OC([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[CH:20]=[C:21]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH3:35])=[CH:26][N:25](S(C4C=CC(C)=CC=4)(=O)=O)[C:22]3=[N:23][CH:24]=2)[CH:14]=1)C(O)=O)=O)(C)(C)C.[CH3:46][NH:47][CH3:48].[CH:49](N(C(C)C)CC)(C)C.[OH-:58].[K+]>CN(C=O)C.CO>[NH2:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:19]2[CH:20]=[C:21]3[C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[O:34][CH3:35])=[CH:26][NH:25][C:22]3=[N:23][CH:24]=2)[CH:14]=1)[C:46]([N:47]([CH3:49])[CH3:48])=[O:58]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 14797Potassium HydroxideHCID 81531DiisopropylethylamineHCID 59825105HCID 59825105, compound

Product 1

HCID 59825095HCID 59825095, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-Butoxycarbonylamino-{3-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-acetic acid (100 mg, 0.16 mmol), dimethylamine (2 N solution in THF, 0.16 mL, 0.32 mmol), diisopropylethylamine (24 mg, 0.19 mmol) in DMF (1 mL) was added O-(7-azabenzotriazol-1-yl)-N,N,N′,N′,-tetramethyluromiumhexafluorophosphate (73 mg, 0.19 mmol). The resulting solution was stirred at room temperature for 1 hour. Methanol (1 mL) and potassium hydroxide (50% in water, 0.2 mL) were added and the resulting mixture was stirred for 30 minutes. The mixture was concentrated in GeneVac at 60° C. for 2 hours. To the residue was added trifluoroacetic acid (1 mL) and the resulting mixture was sonicated till the residue is completely dissolved. The solution was concentrated and the residue was taken up in DMSO (2 mL) and purified with reverse phase preparative LCMS to afford 2-Amino-2-{3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-N,N-dimethyl-acetamide as a pale yellow solid (23 mg, 35%). MS: m/z 401 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 2.86 (s, 3H), 2.93 (s, 3H), 3.84 (s, 3H), 5.14 (s, 1H), 7.05 (t, 1H), 7.15 (d, 1H), 7.31 (dt, 1H), 7.35 (d, 1H), 7.48 (t, 1H), 7.58 (dd, 1H), 7.68 (d, 1H), 7.73 (s, 1H), 7.74 (s, 1H), 8.16 (d, 1H), 8.54 (d, 1H), 11.95 (s, 1H).

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. concentrationThe mixture was concentrated in GeneVac at 60° C. for 2 hours
  3. additionTo the residue was added trifluoroacetic acid (1 mL)
  4. customthe resulting mixture was sonicated till the residue
  5. dissolutionis completely dissolved
  6. concentrationThe solution was concentrated
  7. custompurified with reverse phase preparative LCMS

Sources & evidence

ORD record
ord-4524303f698f48abad88ef9fdaa0a5a0
Source dataset
uspto-grants-2012_08
Patent number
US08242280B2

Reaction notes

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