Triethylamine → HCID 57242608, compound

HRID 357201Notes

Reaction equation

HRID 357201 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([S:10][CH2:11][CH2:12][CH2:13][C:14]([OH:16])=O)=[CH:8][CH:7]=[CH:6][C:5]=12.C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.C(N(CC)CC)C.Cl.[O:46]=[S:47]1(=[O:69])[CH2:52][CH2:51][CH2:50][N:49]2[C:53](=[O:68])[N:54]([CH2:64][CH2:65][CH2:66][NH2:67])[C:55](=[O:63])[C:56]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[C:48]12>O.ClCCl>[O:69]=[S:47]1(=[O:46])[CH2:52][CH2:51][CH2:50][N:49]2[C:53](=[O:68])[N:54]([CH2:64][CH2:65][CH2:66][NH:67][C:14](=[O:16])[CH2:13][CH2:12][CH2:11][S:10][C:9]3[N:4]4[CH:3]=[CH:2][N:1]=[C:5]4[CH:6]=[CH:7][CH:8]=3)[C:55](=[O:63])[C:56]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[C:48]12

Participants

8

Reactant 5

HCID 8471Triethylamine2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18936677HCID 18936677, compoundHCID 18936872HCID 18936872, compound

Product 1

HCID 57242608HCID 57242608, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a dichloromethane solution of 590 mg (2.5 mmol) of 4-(imidazo[1,2-a]pyridine-5-ylthio)butanoic acid and 383 mg (2.5 mmol) of HOBt, 479 mg (2.5 mmol) of WSC and 0.42 ml (3 mmol) of triethylamine were added. After the reaction mixture was stirred at 0° C. for 1.5 hours, 1.158 g (3 mmol) of 3-(1,1,6,8-tetraoxo-9-phenyl-2,3,4,8-tetrahydropyrimido[6,1-b][1,3]thiazin-7-yl)propylamine hydrochloride and 0.84 ml (6 mmol) of triethylamine were added, followed by stirring at room temperature for 16 hours. After water was added, the mixture was extracted with dichloromethane and dried, after which the solvent was distilled off. The residue was purified by column chromatography (eluent, chloroform→chloroform/methanol=25/1) to yield 683.9 mg (48.2%, white oily substance) of the desired product.

Workup

  1. stirringby stirring at room temperature for 16 hours
  2. extractionthe mixture was extracted with dichloromethane
  3. customdried
  4. distillationafter which the solvent was distilled off
  5. customThe residue was purified by column chromatography (eluent, chloroform→chloroform/methanol=25/1)

Sources & evidence

ORD record
ord-bc416afbdb5f4f67a083c1ba68d24c53
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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