Triethylamine → HCID 178521437, compound

HRID 870561Notes

Reaction equation

HRID 870561 reaction equation
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11]1[N:12]=[CH:13][C:14]2[CH2:20][NH:19][CH2:18][CH2:17][C:15]=2[N:16]=1.[NH:21]1[C:25]([CH2:26][CH2:27][O:28][CH2:29][C:30](O)=[O:31])=[CH:24][N:23]=[N:22]1.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N)C.C(N(CC)CC)C>ClCCl>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[NH:10][C:11]1[N:12]=[CH:13][C:14]2[CH2:20][N:19]([C:30](=[O:31])[CH2:29][O:28][CH2:27][CH2:26][C:25]3[N:21]=[N:22][NH:23][CH:24]=3)[CH2:18][CH2:17][C:15]=2[N:16]=1

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 21883477Ethylcarbodiimide hydrochlorideHCID 86726522N-(indan-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amineHCID 178525980HCID 178525980, compound

Product 1

HCID 178521437HCID 178521437, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add N-indan-2-yl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-2-amine (4.2 g, 15.8 mmol) to a mixture of 2-[2-(1H-triazol-5-yl)ethoxy]acetic acid (2.7 g, 15.8 mmol), 1-hydroxybenzotriazole (3.20 g, 23.7 mmol), and dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.44 g, 28.4 mmol) in dichloromethane (40 mL) at 25° C. Add triethylamine (4.40 mL, 31.6 mmol) to the reaction mixture and stir for 16 h. Wash with water (2×50 mL) and concentrate the organic layer. Purify by silica gel column chromatography, eluting with ethyl acetate/methanol, to give the title compound (4.0 g, 60%) as a solid. MS (m/z): 420 (M+H).

Workup

  1. washWash with water (2×50 mL)
  2. concentrationconcentrate the organic layer
  3. customPurify by silica gel column chromatography
  4. washeluting with ethyl acetate/methanol

Sources & evidence

ORD record
ord-73b9e2cb4c3e46faaad2515cbd98f9ea
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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