Formaldehyde → HCID 117699430, compound

HRID 1049826Notes

Reaction equation

HRID 1049826 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH2:14][S:15]([N:18]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[C:32](=[O:33])[CH2:31][C:30](=[O:34])[NH:29][C:28]4[C:35]5[C:40]([CH:41]=[CH:42][C:27]3=4)=[CH:39][CH:38]=[CH:37][CH:36]=5)=[CH:22][CH:21]=2)[CH3:19])(=[O:17])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH2:9]1.[CH2:43]=O.[C:45]([BH3-])#[N:46].[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[CH3:43][N:46]([CH3:45])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1([CH2:14][S:15]([N:18]([C:20]2[CH:25]=[CH:24][C:23]([N:26]3[C:32](=[O:33])[CH2:31][C:30](=[O:34])[NH:29][C:28]4[C:35]5[C:40]([CH:41]=[CH:42][C:27]3=4)=[CH:39][CH:38]=[CH:37][CH:36]=5)=[CH:22][CH:21]=2)[CH3:19])(=[O:17])=[O:16])[CH:13]=[CH:12][CH:11]=[CH:10][CH2:9]1

Participants

6

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 117699228HCID 117699228, compound

Product 1

HCID 117699430HCID 117699430, compoundYield 42%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

1-(2-Aminophenyl)-N-[4-(2,4-dioxo-1,2,3,4-tetrahydronaphtho[1,2-b][1,4]diazepin-5-yl)phenyl]phenyl-N-methylmethanesulfonamide (18 mg, 0.036 mmol) mentioned above, zinc chloride (12 mg, 0.090 mmol), formalin (2.7 mg, 0.090 mmol), and sodium cyanoborohydride (5.7 mg, 0.090 mmol) were dissolved in methanol, and the solution was refluxed by heating for 5 hours under a nitrogen atmosphere. After the disappearance of the starting materials was confirmed, the reaction mixture was treated in a conventional manner to give the title compound (8 mg, yield 42%) as white crystals.

Workup

  1. temperaturethe solution was refluxed
  2. temperatureby heating for 5 hours under a nitrogen atmosphere
  3. additionthe reaction mixture was treated in a conventional manner

Sources & evidence

ORD record
ord-2c39ebbde6e5488b8c78b44784faa4f0
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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