1,2-Dichloroethane → HCID 57819877, compound

HRID 657422Notes

Reaction equation

HRID 657422 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.[CH3:23][C:24]([CH3:32])([CH2:28][C:29]([OH:31])=[O:30])[C:25]([OH:27])=[O:26].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>C(Cl)Cl>[CH2:14]([N:11]1[C:6]2=[N:7][C:8]([CH2:9][CH3:10])=[C:3]([CH2:2][NH:1][C:29](=[O:30])[CH2:28][C:24]([CH3:32])([CH3:23])[C:25]([OH:27])=[O:26])[C:4]([NH:16][CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[C:5]2[CH:13]=[N:12]1)[CH3:15].[CH2:14]([N:11]1[C:6]2=[N:7][C:8]([CH2:9][CH3:10])=[C:3]([CH2:2][NH:1][C:25](=[O:26])[C:24]([CH3:32])([CH3:23])[CH2:28][C:29]([OH:31])=[O:30])[C:4]([NH:16][CH:17]3[CH2:18][CH2:19][O:20][CH2:21][CH2:22]3)=[C:5]2[CH:13]=[N:12]1)[CH3:15]

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 117012,2-Dimethylsuccinic acidHCID 757711-HydroxybenzotriazoleHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Product 2

HCID 57819877HCID 57819877, compoundYield 55.6%HCID 57819884HCID 57819884, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

174(a) 5-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (303.0 mg, 1.0 mmol) and 2,2-dimethylbutanedioic acid (146.0 mg, 1.0 mmol) were dissolved in DCM (10 mL), followed by the addition of HOBt (1.0 eq, 153.0 mg) and EDC (1.0 eq, 192.0 mg). The resultant solution was stirred overnight. The solution was purified by reverse phase HPLC using a Gilson to yield 4-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-2,2-dimethyl-4-oxobutanoic acid and 4-({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)-3,3-dimethyl-4-oxobutanoic acid mixture 120 mg.

Workup

  1. customThe solution was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-f64c5c6dd2034cfeb4dd8e52ee18202d
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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