Formaldehyde → HCID 178461059, compound

HRID 1943894Notes

Reaction equation

HRID 1943894 reaction equation
C=O.[F:3][C:4]1[C:27]([NH:28][S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])=[CH:26][CH:25]=[C:24]([F:35])[C:5]=1[C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:17]([C:18]3[CH2:19][CH2:20][NH:21][CH2:22][CH:23]=3)=[N:16][NH:15][C:12]2=[N:13][CH:14]=1)=[O:7].[CH2:36](Cl)Cl.CO.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CC(O)=O>[F:3][C:4]1[C:27]([NH:28][S:29]([CH2:32][CH2:33][CH3:34])(=[O:31])=[O:30])=[CH:26][CH:25]=[C:24]([F:35])[C:5]=1[C:6]([NH:8][C:9]1[CH:10]=[C:11]2[C:17]([C:18]3[CH2:19][CH2:20][N:21]([CH3:36])[CH2:22][CH:23]=3)=[N:16][NH:15][C:12]2=[N:13][CH:14]=1)=[O:7]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 21226129Dichloromethane methanolHCID 178461056HCID 178461056, compound

Product 1

HCID 178461059HCID 178461059, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

37% Aqueous formaldehyde (100 μL) was added to a solution of 2,6-difluoro-3-(propylsulfonamido)-N-(3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)benzamide (22 mg, 0.046 mmol) in 5:1 CH2Cl2/MeOH (6 mL), followed by a drop of AcOH. After 5 minutes, sodium triacetoxyborohydride (49 mg, 5 equiv) was added, and the reaction mixture was stirred for 2 hours at ambient temperature. The reaction mixture was quenched with MeOH, concentrated, and purified by silica gel chromatography (10:90:1 MeOH/CHCl3/NH4OH) to afford 2,6-difluoro-N-(3-(1-methyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-pyrazolo[3,4-b]pyridin-5-yl)-3-(propylsulfonamido)benzamide as a white solid (14 mg, 62%). 1H NMR (400 MHz, CD3OD) δ 8.90-8.88 (m, 1H), 8.62-8.60 (m, 1H), 7.70-7.63 (m, 1H), 7.17-7.11 (m, 1H), 6.57-6.53 (m, 1H), 3.35-3.31 (m, 2H), 3.14-3.09 (m, 2H), 2.90-2.83 (m, 4H), 2.49 (s, 3H), 1.92-1.82 (m, 2H), 1.08-1.04 (m, 3H); m/z (APCI-pos) M+1=491.0.

Workup

  1. customThe reaction mixture was quenched with MeOH
  2. concentrationconcentrated
  3. custompurified by silica gel chromatography (10:90:1 MeOH/CHCl3/NH4OH)

Sources & evidence

ORD record
ord-730bdcb4f5824b48a10dba65ab306d7b
Source dataset
uspto-grants-2013_03
Patent number
US08394795B2

Reaction notes

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