Triethylamine → HCID 10364072, compound

HRID 2293917Notes

Reaction equation

HRID 2293917 reaction equation
Cl[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[N:3]=1.COC(=O)CN.[CH2:27]([N:29](CC)[CH2:30]C)C>CN(C=O)C>[CH3:27][N:29]([CH3:30])[C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH3:11])=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([I:20])[CH:15]=2)[N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 69221Glycine methyl esterHCID 10340909HCID 10340909, compound

Product 1

HCID 10364072HCID 10364072, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of compound 6 (40 mg, 0.1 mmol), glycine methyl ester (310 mg, 2.47 mmol), and triethylamine (0.7 mL, 5.0 mmol) in DMF (2 mL) was heated for 22 h at room temperature. After cooling, the mixture was evaporated to dryness and purified on a silica gel column (chloroform-methanol, 20:1) to give compound 12 (25 mg, 53.5%) as a colorless solid. 1H NMR (DMSO-d6) δ 3.06 (s, 6 H, N(CH3)2), 3.58 (s, 3 H, 9-CH3), 4.55 (br s, 2 H, CH2), 7.10 (pseudo t, J=8.0 and 7.6 Hz, 1 H, H-16), 7.38 (d, J=7.7 Hz, 1 H, H-17), 7.56 (d, J=8.0 Hz, 1 H, H-15), 7.70 (s, 1 H, H-13), 7.77 (s, 1 H, H-8), 7.92 (br s, 1 H, exchangeable with D2O, NH).

Workup

  1. temperatureAfter cooling
  2. customthe mixture was evaporated to dryness
  3. custompurified on a silica gel column (chloroform-methanol, 20:1)

Sources & evidence

ORD record
ord-6272f07e2b6a4d5b9b30df4255b66fa5
Source dataset
uspto-grants-1997_11
Patent number
US05688774

Reaction notes

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