Triethylamine → 2-chloro-5-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)sulfonyl]-4-fluorobenzoic acid

HRID 564646Notes

Reaction equation

HRID 564646 reaction equation
[NH2:1][CH2:2][C:3]1[C:8]([CH2:9][CH3:10])=[N:7][C:6]2[N:11]([CH2:14][CH3:15])[N:12]=[CH:13][C:5]=2[C:4]=1[NH:16][CH:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.[Cl:23][C:24]1[CH:32]=[C:31]([F:33])[C:30]([S:34](Cl)(=[O:36])=[O:35])=[CH:29][C:25]=1[C:26]([OH:28])=[O:27].CCN(CC)CC>C(Cl)Cl>[Cl:23][C:24]1[CH:32]=[C:31]([F:33])[C:30]([S:34]([NH:1][CH2:2][C:3]2[C:4]([NH:16][CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[C:5]3[CH:13]=[N:12][N:11]([CH2:14][CH3:15])[C:6]3=[N:7][C:8]=2[CH2:9][CH3:10])(=[O:36])=[O:35])=[CH:29][C:25]=1[C:26]([OH:28])=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 45719302-Chloro-5-chlorosulfonyl-4-fluorobenzoic acidHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Product 1

HCID 578132602-chloro-5-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)sulfonyl]-4-fluorobenzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

345(a) 5-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (30.0 mg, 0.1 mmol) and 2-chloro-5-(chlorosulfonyl)-4-fluorobenzoic acid (0.1 mmol) was dissolved in DCM (3 mL), followed by the addition of Et3N (10 mg, 0.1 mmol). The resultant solution was stirred overnight. The solution was then purified using a Gilson to give 2-chloro-5-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)sulfonyl]-4-fluorobenzoic acid.

Workup

  1. customThe solution was then purified

Sources & evidence

ORD record
ord-aff66d44115140738b906061328150e4
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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