Acetic Acid → HCID 69266952, compound

HRID 917651Notes

Reaction equation

HRID 917651 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[CH2:17][OH:18])[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH:23]=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(=O)([O-])O.[Na+].ClCCCl>[Cl:19][C:20]1[CH:21]=[C:22]([CH:25]=[CH:26][C:27]=1[O:28][CH3:29])[CH2:23][NH:1][C:2]1[N:3]=[C:4]([N:12]2[CH2:16][CH2:15][CH2:14][CH:13]2[CH2:17][OH:18])[S:5][C:6]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 786193-Chloro-4-methoxybenzaldehydeHCID 5049666Sodium triacetoxyborohydride2×HCID 69272835HCID 69272835, compound

Product 1

HCID 69266952HCID 69266952, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a mixture of 4-amino-5-ethoxycarbonyl-2-(2-hydroxymethyl-1-pyrrolodinyl)thiazole (prepared in the above (2)) 177 mg, 3-chloro-4-methoxybenzaldehyde 111 mg, acetic acid 78 mg and 1,2-dichloroethane 8 ml is added sodium triacetoxyborohydride 415 mg, and the mixture is stirred at room temperature for 6 hours. Further 3-chloro-2 5 4-methoxybenzaldehyde 111 mg and sodium triacetoxyborohydride 415 mg are added thereto, and the mixture is stirred at room temperature for 3 days. The reaction mixture is diluted with an aqueous sodium hydrogen carbonate solution and the organic layer is washed, dried and concentrated in vacuo. The residue is separated with reversed phase column chromatography and preparative thin-layer chromatography, and then triturated with ether to give 4-(3-chloro-4-methoxybenzylamino)-5-ethoxycarbonyl-2-(2-hydroxymethyl-1-pyrrolodinyl)thiazole as crystals, 171 mg. mp 103.5-104.5° C.

Workup

  1. stirringthe mixture is stirred at room temperature for 3 days
  2. washthe organic layer is washed
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue is separated with reversed phase column chromatography
  6. customtriturated with ether

Sources & evidence

ORD record
ord-3d67d124a3d74e2a898e1431c73c04ef
Source dataset
uspto-grants-2007_09
Patent number
US07273868B2

Reaction notes

Loading…