Formaldehyde → HCID 59577341, compound

HRID 1773410Notes

Reaction equation

HRID 1773410 reaction equation
[NH:1]1[CH2:4][CH:3]([CH2:5][NH:6][C:7]2[CH:33]=[C:32]([N:34]3[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]3)[CH:31]=[CH:30][C:8]=2[C:9]([NH:11][C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([CH2:21][C:22]4[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[CH:23]=4)[CH:19]=3)[NH:14][N:13]=2)=[O:10])[CH2:2]1.C=O.O.[C:44](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[F:28][C:26]1[CH:27]=[C:22]([CH:23]=[C:24]([F:29])[CH:25]=1)[CH2:21][C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][CH:17]=1)[NH:14][N:13]=[C:12]2[NH:11][C:9](=[O:10])[C:8]1[CH:30]=[CH:31][C:32]([N:34]2[CH2:35][CH2:36][N:37]([CH3:40])[CH2:38][CH2:39]2)=[CH:33][C:7]=1[NH:6][CH2:5][CH:3]1[CH2:2][N:1]([CH3:44])[CH2:4]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 962WaterHCID 5049666Sodium triacetoxyborohydrideHCID 59577332HCID 59577332, compound

Product 1

HCID 59577341HCID 59577341, compoundYield 6.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 2-[(azetidin-3-ylmethyl)amino]-N-[5-(3,5-difluorobenzyl)-1H-indazol-3-yl]-4-(4-methylpiperazin-1-yl)benzamide (100 mg, 0.14 mmol) in dichloromethane (2 mL) were added formaldehyde 37 wt. % in water (0.014 mL, 0.168 mmol), TEA (0.4 mmol) and sodium triacetoxyborohydride (45 mg, 0.21 mmol). The mixture was stirred at room temperature overnight, diluted with dichloromethane, washed with aqueous NaHCO3 sat.sol., water and brine. Organic phase was dried over sodium sulfate and evaporated to dryness. The crude was purified by flash chromatography on silica gel using dichloromethane/methanol/NH3 5N in MeOH 100:10:1 as the eluant, affording 5 mg of the title compound.

Workup

  1. washwashed with aqueous NaHCO3
  2. dry with materialOrganic phase was dried over sodium sulfate
  3. customevaporated to dryness
  4. customThe crude was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d4ecffe19bcb4fd18dc6afdd59857843
Source dataset
uspto-grants-2016_02
Patent number
US09255087B2

Reaction notes

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