Trimethylsilyl isocyanate → HCID 67272421, compound

HRID 1592473Notes

Reaction equation

HRID 1592473 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH2:16][C:17]1[C:22]([C:23]([O:26][C:27](=[O:29])[CH3:28])([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][N:18]=1)[CH2:7][C:8]1[C:13]([CH3:14])=[CH:12][C:11]([CH3:15])=[CH:10][N:9]=1.C[Si]([N:34]=[C:35]=[O:36])(C)C>CC(O)C>[CH3:14][C:13]1[C:8]([CH2:7][N:6]([CH2:16][C:17]2[C:22]([C:23]([O:26][C:27](=[O:29])[CH3:28])([CH3:25])[CH3:24])=[CH:21][CH:20]=[CH:19][N:18]=2)[CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:35]([NH2:34])=[O:36])=[N:9][CH:10]=[C:11]([CH3:15])[CH:12]=1

Participants

4

Reactant 2

HCID 70696Trimethylsilyl isocyanateHCID 11165441HCID 11165441, compound

Product 1

HCID 67272421HCID 67272421, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of acetic acid 1-(2-{[(4-amino-butyl)-(3,5-dimethyl-pyridin-2-ylmethyl)-amino]-methyl}-pyridin-3-yl)-1-methyl-ethyl ester (223 mg, 0.56 mmol) in i-PrOH (3.7 mL) and treated with trimethylsilylisocyanate (110 μL, 0.78 mmol) at room temperature for 16 hours. The solution was then concentrated under reduced pressure and dried in vacuo. The crude material was then purified by column chromatography with silica gel (20:1:1 CH2Cl2/MeOH/NH4OH) to give almost pure acetic acid 1-(2-{[(3,5-dimethyl-pyridin-2-ylmethyl)-(4-ureido-butyl)-amino]-methyl}-pyridin-3-yl)-1-methyl-ethyl ester as a colorless oil (227 mg, 92%).

Workup

  1. concentrationThe solution was then concentrated under reduced pressure
  2. customdried in vacuo
  3. customThe crude material was then purified by column chromatography with silica gel (20:1:1 CH2Cl2/MeOH/NH4OH)

Sources & evidence

ORD record
ord-1877b2dc6e2142e08ff0c6be044bde68
Source dataset
uspto-grants-2007_11
Patent number
US07291631B2

Reaction notes

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