Triethylamine → HCID 86683394, compound

HRID 579425Notes

Reaction equation

HRID 579425 reaction equation
Br.[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:13]=[O:14])[CH2:9][NH:8][CH2:7][CH2:6]2.C(N(CC)CC)C.[CH3:22][N:23]1[CH2:28][CH2:27][N:26]([CH2:29][CH2:30][C:31](O)=[O:32])[CH2:25][CH2:24]1.Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>O1CCCC1>[OH:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[CH:13]=[O:14])[CH2:9][N:8]([C:31](=[O:32])[CH2:30][CH2:29][N:26]1[CH2:25][CH2:24][N:23]([CH3:22])[CH2:28][CH2:27]1)[CH2:7][CH2:6]2

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 13953803-(4-methylpiperazin-1-yl)propanoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 86683392HCID 86683392, compound

Product 1

HCID 86683394HCID 86683394, compoundYield 21.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of 6-hydroxy-1,2,3,4-tetrahydro-isoquinoline-7-carbaldehyde hydrobromide (82 mg, 0.46 mmol) and triethylamine (322 μL, 234 mg, 2.3 mmol) in anhydrous tetrahydrofuran (2 mL), 3-(4-methyl-piperazin-1-yl)-propionic acid (80 mg, 0.46 mmol), (3-dimethylamino-propyl)-ethyl-carbodiimide hydrochloride (98 mg, 0.51 mmol) and 1-hydroxybenzotriazole (69 mg, 0.51 mmol) were added in the above order and the mixture was stirred at room temperature for 7 h. After evaporation, the residue was taken up in chloroform (10 mL) and washed with sat NaHCO3 (2×5 mL) and brine (5 mL). The organic phase was dried over MgSO4 and evaporated. The obtained crude product (94 mg) was purified by column chromatography on silica gel, eluting with CHCl3/MeOH 94/6 mixture. In this manner the title compound (33 mg, 0.10 mmol, 21%) was obtained.

Workup

  1. additionwere added in the above order
  2. customAfter evaporation
  3. washwashed
  4. dry with materialThe organic phase was dried over MgSO4
  5. customevaporated
  6. customThe obtained crude product (94 mg)
  7. customwas purified by column chromatography on silica gel
  8. washeluting with CHCl3/MeOH 94/6 mixture

Sources & evidence

ORD record
ord-ac0d1a58ad1c42f5813081f9e6140bf0
Source dataset
uspto-grants-2015_05
Patent number
US09040714B2

Reaction notes

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