Formaldehyde → HCID 66755273, compound

HRID 1643973Notes

Reaction equation

HRID 1643973 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([S:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)(=[O:12])=[O:11])[C:8](=[O:21])[N:7]([CH:22]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:23]([NH:25][CH2:26][CH2:27][N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[O:24])[C:6]=2[CH:40]=1.C=O.[C:43](O[BH-](OC(=O)C)OC(=O)C)(=O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:9]([S:10]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)(=[O:11])=[O:12])[C:8](=[O:21])[N:7]([CH:22]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:23]([NH:25][CH2:26][CH2:27][N:28]3[CH2:29][CH2:30][N:31]([CH3:43])[CH2:32][CH2:33]3)=[O:24])[C:6]=2[CH:40]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 2724942TriacetoxyborohydrideHCID 66754850HCID 66754850, compound

Product 1

HCID 66755273HCID 66755273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 98.0 mg (0.17 mmol) 2-[6-chloro-3-(4-methoxybenzenesulfonyl)-2-oxo-2,3-dihydrobenzimidazol-1-yl]-2-phenyl-N-(2-piperazin-1-yl-ethyl)acetamide (Example 131) in 4 ml of THF was mixed with 5.54 mg (0.19 mmol) of paraformaldehyde and 170 mg of MP-triacetoxyborohydride resin (Argonaut, 2.55 mmol/g, 0.42 mmol) and shaken at room temperature overnight. The solid phase reagent was filtered off and washed with dichloromethane. The filtrate was concentrated under reduced pressure.

Workup

  1. filtrationThe solid phase reagent was filtered off
  2. washwashed with dichloromethane
  3. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-5194df0bd2d64a15bdd01bfcfa12f6bb
Source dataset
uspto-grants-2012_02
Patent number
US08119676B2

Reaction notes

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