Water → HCID 58423337, compound

HRID 1398019Notes

Reaction equation

HRID 1398019 reaction equation
C[N:2]([CH3:26])[CH:3]1[CH2:7][CH2:6][N:5]([C:8]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[CH:18][C:9]=2/[CH:10]=[C:11]2/[C:12](=[O:17])[NH:13][C:14](=[O:16])[S:15]/2)[CH2:4]1.O=C[CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34].[Na].O>C(Cl)Cl>[O:16]=[C:14]1[NH:13][C:12](=[O:17])/[C:11](=[CH:10]/[C:9]2[CH:18]=[C:19]([O:24][CH3:25])[C:20]([O:22][CH3:23])=[CH:21][C:8]=2[N:5]2[CH2:6][CH2:7][CH:3]([NH:2][CH2:26][CH2:29][NH:30][C:31](=[O:37])[O:32][C:33]([CH3:36])([CH3:35])[CH3:34])[CH2:4]2)/[S:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 4247255tert-butyl N-(2-oxoethyl)carbamateHCID 5360545SodiumHCID 58423342HCID 58423342, compound

Product 1

HCID 58423337HCID 58423337, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (5Z)-5-{2-[3-(dimethylamino)pyrrolidin-1-yl]-4,5-dimethoxybenzylidene}-1,3-thiazolidine-2,4-dione (Example 52) (120 mg, 0.31 mmol) and tert-butyl 2-oxoethylcarbamate (198 mg, 1.24 mmol) in CH2Cl2 (20 mL) were heated to reflux for 15 min followed by the addition of sodium triacetoxyhydroborate (65.9 mg, 0.31 mmol). The reaction mixture was refluxed overnight before being allowed to cool to ambient temperature. Water (˜0.5 mL) was added and the mixture was allowed to stir for 15 min before being loaded onto a silica gel column which was eluted with ethyl acetate/hexane (10:1) to yield the title compound as an orange solid as (60.0 mg, 39.2%); m/z 493.

Workup

  1. temperaturewere heated
  2. temperatureto reflux for 15 min
  3. temperatureThe reaction mixture was refluxed overnight
  4. washwas eluted with ethyl acetate/hexane (10:1)

Sources & evidence

ORD record
ord-6b07b2c9d06d41de959c9037989e6777
Source dataset
uspto-grants-2014_12
Patent number
US08901307B2

Reaction notes

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