Diisopropylethylamine → HCID 58024751, compound

HRID 1675686Notes

Reaction equation

HRID 1675686 reaction equation
F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([NH:35][C:36]1[CH:44]=[CH:43][C:39]([C:40]([OH:42])=O)=[CH:38][CH:37]=1)=[O:34].C(N(CC)C(C)C)(C)C.[NH2:54][CH2:55][C:56]1[C:61]([CH2:62][CH3:63])=[N:60][C:59]2[N:64]([CH2:67][CH3:68])[N:65]=[CH:66][C:58]=2[C:57]=1[NH:69][CH:70]1[CH2:75][CH2:74][O:73][CH2:72][CH2:71]1.C(=O)(O)[O-].[Na+]>CN(C)C=O>[Br:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][C:33]([NH:35][C:36]1[CH:37]=[CH:38][C:39]([C:40]([NH:54][CH2:55][C:56]2[C:57]([NH:69][CH:70]3[CH2:71][CH2:72][O:73][CH2:74][CH2:75]3)=[C:58]3[CH:66]=[N:65][N:64]([CH2:67][CH3:68])[C:59]3=[N:60][C:61]=2[CH2:62][CH3:63])=[O:42])=[CH:43][CH:44]=1)=[O:34]

Participants

7

Reactant 5

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58024763HCID 58024763, compoundHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine2×

Product 1

HCID 58024751HCID 58024751, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

O-(7-Azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (HATU, 2.4 g, 6.3 mmol) was added to a solution of 4-[(8-bromooctanoyl)amino]benzoic acid (2.1 g, 6.1 mmol) in N,N-dimethylformamide (20 ml) followed by N,N-diisopropylethylamine (2.5 g, 19 mmol). The solution was stirred at room temperature for 15 min, and 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (1.7 g, 5.6 mmol. e.g. which can be substantially as prepared in Intermediate 7 including alternative preparation no. 1 thereof) was added as a solid. The solution was stirred at room temperature for 3 hours, and then was added to aqueous sodium bicarbonate solution (200 ml) and extracted with dichloromethane (2×100 ml). The dried (sodium sulphate) organic extract was evaporated gently to leave crude 4-[(8-bromooctanoyl)amino]-N-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}benzamide mixed with N,N-dimethylformamide (about 5 ml).

Workup

  1. addition1 thereof) was added as a solid
  2. stirringThe solution was stirred at room temperature for 3 hours
  3. extractionextracted with dichloromethane (2×100 ml)
  4. dry with materialThe dried (sodium sulphate)
  5. extractionorganic extract
  6. customwas evaporated gently

Sources & evidence

ORD record
ord-0af7e78951f84de1b3e8a054b192b3e0
Source dataset
uspto-grants-2011_08
Patent number
US08003663B2

Reaction notes

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