Acetic Acid → HCID 69266952, compound

HRID 1352798Notes

Reaction equation

HRID 1352798 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-19d97577feb14b19a2993a0537f6b4ed
Source dataset
uspto-grants-2007_05
Patent number
US07220736B2

Reaction notes

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