Dimethyl Sulfoxide → HCID 22598980, compound

HRID 2252462Notes

Reaction equation

HRID 2252462 reaction equation
[NH2:1][CH:2]([CH2:6][NH:7][C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][CH2:20][CH2:21][NH:22][C:23]1[NH:24][CH:25]=[CH:26][N:27]=1)[N:14]=[CH:13]2)=[O:9])[C:3]([OH:5])=[O:4].C(N(CC)CC)C.CS(C)=O.[C:39]([NH:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52](ON1C(=O)CCC1=O)=[O:53])([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40]>CN(C)C=O>[C:42]([O:41][C:39]([NH:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][C:52]([NH:1][CH:2]([CH2:6][NH:7][C:8]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[N:15]([CH2:19][CH2:20][CH2:21][NH:22][C:23]1[NH:24][CH:25]=[CH:26][N:27]=1)[N:14]=[CH:13]2)=[O:9])[C:3]([OH:5])=[O:4])=[O:53])=[O:40])([CH3:45])([CH3:44])[CH3:43]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 5074016Boc-6-Ahx-OSuHCID 22598941HCID 22598941, compound

Product 1

HCID 22598980HCID 22598980, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Amino-3-((1-(3-(imidazol-2-ylamino)propyl)(1H-indazol-5-yl))carbonylamino)propanoic acid (0.050 g, 0.103 mmol) was dissolved in N,N-dimethylformamide (2 mL). Triethylamine (43.1 μL, 0.309 mmol) was added and the reaction was stirred for 5 minutes. A precipitate formed so methyl sulfoxide (1 mL) was added. Succinimidyl N-boc-6-aminohexanoate (0.0406 g, 0.124 mmol) was added and the reaction was stirred under N2 for 18 h. The reaction was then concentrated to an oil under high vacuum. The oil was purified by the following method (Preparative HPLC Method A) to give 39.9 mgs (66%) of product. ESMS: Calcd. for C28H40N8O6, 584.31. Found, 585.2 [M+H]+1. Analytical HPLC, Method B, Rt=18.72 min, Purity=98% Preparative HPLC Method A:

Workup

  1. additionwas added
  2. stirringthe reaction was stirred under N2 for 18 h
  3. concentrationThe reaction was then concentrated to an oil under high vacuum
  4. customThe oil was purified by the following method (Preparative HPLC Method A)

Sources & evidence

ORD record
ord-9ca204cd5feb41859404a81aa9270e9a
Source dataset
uspto-grants-2008_01
Patent number
US07321045B2

Reaction notes

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