Triethylamine → HCID 53634368, compound

HRID 357199Notes

Reaction equation

HRID 357199 reaction equation
[N:1]1[CH:2]=[CH:3][N:4]2[C:9]([CH2:10][C:11]([OH:13])=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:43]=[S:44]1(=[O:66])[CH2:49][CH2:48][CH2:47][N:46]2[C:50](=[O:65])[N:51]([CH2:61][CH2:62][CH2:63][NH2:64])[C:52](=[O:60])[C:53]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[C:45]12>O.ClCCl>[O:66]=[S:44]1(=[O:43])[CH2:49][CH2:48][CH2:47][N:46]2[C:50](=[O:65])[N:51]([CH2:61][CH2:62][CH2:63][NH:64][C:11](=[O:13])[CH2:10][C:9]3[N:4]4[CH:3]=[CH:2][N:1]=[C:5]4[CH:6]=[CH:7][CH:8]=3)[C:52](=[O:60])[C:53]([C:54]3[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=3)=[C:45]12

Participants

8

Reactant 5

HCID 8471Triethylamine2×HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 18936677HCID 18936677, compoundHCID 18936841(Imidazo[1,2-a]pyridin-5-yl)acetic acid

Product 1

HCID 53634368HCID 53634368, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a dichloromethane solution of 601 mg (2.5 mmol) of imidazo[1,2-a]pyridin-5-acetic acid and 383 mg (2.5 mmol) of HOBt, 479 mg (2.5 mmol) of WSC and 0.5 ml (3.6 mmol) of triethylamine were added. After the reaction mixture was stirred at 0° C. for 30 minutes, 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 3 hours and then at 40° C. for 14 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 74.7 mg (5.9%, yellow oily substance) of the desired product.

Workup

  1. stirringby stirring at room temperature for 3 hours
  2. waitat 40° C. for 14 hours
  3. extractionthe mixture was extracted with dichloromethane
  4. customdried
  5. distillationafter which the solvent was distilled off
  6. customThe residue was purified by column chromatography (eluent, chloroform→chloroform/methanol=25/1)

Sources & evidence

ORD record
ord-e5960c1e351a4a61b2dc117a2792d422
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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