Formaldehyde → HCID 11773623, compound

HRID 722713Notes

Reaction equation

HRID 722713 reaction equation
[C:1]([C:3]1[C:11]2[CH2:10][CH2:9][NH:8][CH2:7][C:6]=2[S:5][C:4]=1[NH:12][C:13](=[O:27])[CH:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)#[N:2].C=O.[C:30]([BH3-])#N.[Na+]>CO>[C:1]([C:3]1[C:11]2[CH2:10][CH2:9][N:8]([CH3:30])[CH2:7][C:6]=2[S:5][C:4]=1[NH:12][C:13](=[O:27])[CH:14]([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)#[N:2]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 21886021HCID 21886021, compound

Product 1

HCID 11773623HCID 11773623, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of N-(3-Cyano-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-2,2-diphenyl-acetamide (prepared in Example 8, step 1; 75 mg; 0.15 mmol) and formaldehyde (0.1 mL of 37% solution) in dry methanol at room temperature was added sodium cyanoborohydride (14.5 mg; 0.23 mmol). The mixture was allowed to stir for 1 hour at room temperature then concentrated in vacuo. The residue was taken up into methylene chloride and washed with water. The organic layer was dried (sodium sulfate) and concentrated in vacuo to give 50 mg (85%) of N-(3-Cyano-6-methyl-4,5,6,7-tetrahydro-thieno[2,3-c]pyridin-2-yl)-2,2-diphenyl-acetamide. ES-HRMS m/e calcd for C23H21N3OS (M+H+) 388.1478, found 388.1481.

Workup

  1. concentrationthen concentrated in vacuo
  2. washwashed with water
  3. dry with materialThe organic layer was dried (sodium sulfate)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d98a7e4038584c7a99207afbea220db4
Source dataset
uspto-grants-2006_11
Patent number
US07138529B2

Reaction notes

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