Methylamine → HCID 69424164, compound

HRID 1351733Notes

Reaction equation

HRID 1351733 reaction equation
[C:1]([Si:5]([CH3:23])([CH3:22])[O:6][CH2:7][CH2:8][C:9]1[C:17]2[C:16]([C:18](O)=[O:19])=[CH:15][CH:14]=[C:13]([CH3:21])[C:12]=2[NH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C[CH2:25][N:26]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.CN>CN(C=O)C.O>[CH3:25][NH:26][C:18]([C:16]1[C:17]2[C:9]([CH2:8][CH2:7][O:6][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:23])[CH3:22])=[CH:10][NH:11][C:12]=2[C:13]([CH3:21])=[CH:14][CH:15]=1)=[O:19]

Participants

8

Reactant 5

HCID 6329MethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 21099145HCID 21099145, compound

Product 1

HCID 69424164HCID 69424164, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-7-methyl-1H-indole-4-carboxylic acid (150 mg, 0.45 mmol), EDCI (104 mg, 0.54 mmol) and HOBt (91.2 mg, 0.68 mmol) in DMF (3 mL) was added diisopropylethylamine (0.39 mL, 2.25 mmol) at room temperature. A solution of methylamine (0.45 mL of 2.0 M in THF, 0.90 mmol) was added to the mixture and the mixture was stirred overnight at room temperature. The solution was diluted with H2O (5 mL) and extracted with EtOAc (3×10 mL). The organic solution was washed brine (20 mL), dried (Na2SO4) and concentrated. The residue was purified by flash chromatography (silica, 40% EtOAc in hexanes) to give 140 mg (90%) of title compound as a pale yellow solid. 1H NMR (CDCl3): 300 MHz δ 8.28 (bs, 1H), 7.20 (m, 2H), 7.00 (d, J=7.35 Hz, 1H), 6.40 (bs, 1H), 3.91 (t, J=6.41 Hz, 2H), 3.08 (m, 5H), 2.54 (s, 3H), 0.88 (s, 9H), −0.08 (s, 6H).

Workup

  1. extractionextracted with EtOAc (3×10 mL)
  2. washThe organic solution was washed brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography (silica, 40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-4b82beeb18c94bda8c35319545dcaac0
Source dataset
uspto-grants-2007_05
Patent number
US07217730B2

Reaction notes

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