Dimethylamine → HCID 57731589, compound

HRID 2234697Notes

Reaction equation

HRID 2234697 reaction equation
C(OC([NH:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]3[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])=[CH:27][N:26](S(C4C=CC(C)=CC=4)(=O)=O)[C:23]3=[N:24][CH:25]=2)[CH:15]=1)C(O)=O)=O)(C)(C)C.[CH3:47][NH:48][CH3:49].[CH:50](N(C(C)C)CC)(C)C.[OH-:59].[K+]>CN(C=O)C.CO>[NH2:8][CH:9]([CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]3[C:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])=[CH:27][NH:26][C:23]3=[N:24][CH:25]=2)[CH:15]=1)[C:47]([N:48]([CH3:50])[CH3:49])=[O:59]

Participants

7

Reactant 4

HCID 674DimethylamineHCID 14797Potassium HydroxideHCID 81531DiisopropylethylamineHCID 57731571HCID 57731571, compound

Product 1

HCID 57731589HCID 57731589, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-tert-butoxycarbonylamino-3-{3-[3-(2-methoxy-phenyl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-propionic 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′,N′-tetramethyluronium hexafluorophosphate (73 mg, 0.19 mmol). The resulting solution was stirred at room temperature for 1 hour. Methanol (1 mL) and potassium hydroxide (50% w/v in water, 0.2 mL) were added and the resulting mixture was stirred for 30 minutes. The mixture was concentrated under reduced pressure. To the residue was added trifluoroacetic acid (1 mL) and the resulting mixture was sonicated until the residue is completely dissolved. The solution was concentrated and the residue purified by mass-triggered reverse-phase HPLC to afford 2-amino-3-{3-[3-(2-methoxy-phenyl)-1H-pyrrolo[2,3-b]pyridin-5-yl]-phenyl}-N,N-dimethyl-propionamide as a pale yellow solid (23 mg, 35%). MS: m/z 415 (M+H+). 1H NMR (500 MHz, DMSO-d6) δ 2.77 (s, 3H), 2.82 (s, 3H), 2.77 (dd, 1H), 2.89 (dd, 1H), 3.84 (s, 3H), 7.05 (t, 1H), 7.14 (d, 1H), 7.19 (d, 1H), 7.30 (dt, 1H), 7.38 (t, 1H), 7.53 (s, 1H), 7.56 (d, 1H), 7.585 (dd, 1H), 7.73 (d, 1H), 8.15 (d, 1H), 8.53 (d, 1H), 11.87 (s, 1H).

Workup

  1. stirringthe resulting mixture was stirred for 30 minutes
  2. concentrationThe mixture was concentrated under reduced pressure
  3. additionTo the residue was added trifluoroacetic acid (1 mL)
  4. customthe resulting mixture was sonicated until the residue
  5. dissolutionis completely dissolved
  6. concentrationThe solution was concentrated
  7. customthe residue purified by mass-triggered reverse-phase HPLC

Sources & evidence

ORD record
ord-91d8926342fb4419bb0fff786c37f9d4
Source dataset
uspto-grants-2010_05
Patent number
US07709645B2

Reaction notes

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