Acetic Acid → HCID 67267117, compound

HRID 602516Notes

Reaction equation

HRID 602516 reaction equation
[CH2:1]([O:4][C:5](=[O:15])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][C:8]=1[CH3:14])[CH2:2][CH3:3].[CH3:16][N:17]([CH3:30])[C:18]1[CH:29]=[CH:28][C:21]2[S:22][C:23]([CH:26]=O)=[C:24]([CH3:25])[C:20]=2[CH:19]=1.C([BH3-])#N.[Na+].C(O)(=O)C>C(#N)C.CO>[CH2:1]([O:4][C:5](=[O:15])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:26][C:23]2[S:22][C:21]3[CH:28]=[CH:29][C:18]([N:17]([CH3:16])[CH3:30])=[CH:19][C:20]=3[C:24]=2[CH3:25])=[CH:9][C:8]=1[CH3:14])[CH2:2][CH3:3]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5003444Sodium cyanoborohydrideHCID 56953891HCID 56953891, compoundHCID 86607170HCID 86607170, compound

Product 1

HCID 67267117HCID 67267117, compoundYield 77.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of (4-amino-2-methylphenyl)-carbamic acid propyl ester (21 mg, 0.10 mmol) and 5-dimethylamino-3-methyl-benzo[b]thiophene-2-carbaldehyde (26 mg, 0.12 mmol) in acetonitrile (0.5 mL) was heated at 170° C. for 2 minutes using a Personal Chemistry Smith Synthesizer microwave device. After cooling to room temperature, a solution of sodium cyanoborohydride (25 mg, 0.40 mmol) in methanol (0.1 mL) was added followed by acetic acid (50 μL), and the mixture was stirred for 30 minutes. It was partitioned between saturated aqueous sodium bicarbonate (10 mL) and ethyl acetate (10 mL), and the organic layer was dried over sodium sulfate and evaporated. Preparative LC-MS afforded the title compound (32 mg, 77% yield).

Workup

  1. customIt was partitioned between saturated aqueous sodium bicarbonate (10 mL) and ethyl acetate (10 mL)
  2. dry with materialthe organic layer was dried over sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-408200737f2c4dec9f8c976d07b8de5a
Source dataset
uspto-grants-2011_03
Patent number
US07906537B2

Reaction notes

Loading…