Formaldehyde → HCID 68514688, compound

HRID 2241345Notes

Reaction equation

HRID 2241345 reaction equation
[CH3:1][O:2][C:3]1[CH:49]=[CH:48][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]5[C:28](=[O:40])[N:29]([C:33]6[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=6)[N:30]=[CH:31][CH:32]=5)=[O:26])=[CH:20][C:19]=4[F:41])=[C:11]3[C:10]([CH:42]3[CH2:47][CH2:46][NH:45][CH2:44][CH2:43]3)=[N:9]2)=[CH:5][CH:4]=1.C=O.[C:52](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:41][C:19]1[CH:20]=[C:21]([NH:24][C:25]([C:27]2[C:28](=[O:40])[N:29]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][CH:34]=3)[N:30]=[CH:31][CH:32]=2)=[O:26])[CH:22]=[CH:23][C:18]=1[O:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:49][CH:48]=3)[N:9]=[C:10]([CH:42]3[CH2:47][CH2:46][N:45]([CH3:52])[CH2:44][CH2:43]3)[C:11]=12

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68513730HCID 68513730, compound

Product 1

HCID 68514688HCID 68514688, compoundYield 79.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A round-bottomed flask was charged with N-(4-(1-(4-methoxybenzyl)-3-(piperidin-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorophenyl)-2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxamide (20.0 mg, 0.0301 mmol), formaldehyde (0.905 mg, 0.0301 mmol), sodium triacetoxyborohydride (6.39 mg, 0.0301 mmol) and CH2Cl2 (10 mL). The reaction mixture was stirred at ambient temperature for 2 days. Then the reaction was partitioned between EtOAc and H2O. The phases were separated and the aqueous phase was re-extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated to yield a crude product. The crude product was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1, v/v) to afford product (16.3 mg, 79.8%). LRMS (APCI pos): >99% purity, 254 nm, m/e 678 (M+1).

Workup

  1. customThen the reaction was partitioned between EtOAc and H2O
  2. customThe phases were separated
  3. extractionthe aqueous phase was re-extracted with EtOAc
  4. dry with materialThe combined organic layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a crude product
  8. customThe crude product was purified by silica gel chromatography (DCM/7 M NH3 in MeOH from 100/1 to 10/1

Sources & evidence

ORD record
ord-10c5a28efdc64af1b861fcbb4cd7fda4
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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