1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59452214, compound

HRID 2381150Notes

Reaction equation

HRID 2381150 reaction equation
CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.[F:22][C:23]1[CH:41]=[C:40]([I:42])[CH:39]=[CH:38][C:24]=1[CH2:25][N:26]1[C:30]2=[CH:31][N:32]=[CH:33][CH:34]=[C:29]2[CH:28]=[C:27]1[C:35]([O-])=[O:36].[Na+].[CH3:44][C:45]1([CH3:53])[O:49][C@@H:48]([CH2:50][O:51][NH2:52])[CH2:47][O:46]1.CCN(C(C)C)C(C)C>C1COCC1.ClCCl.C(OCC)(=O)C>[CH3:44][C:45]1([CH3:53])[O:49][C@@H:48]([CH2:50][O:51][NH:52][C:35]([C:27]2[N:26]([CH2:25][C:24]3[CH:38]=[CH:39][C:40]([I:42])=[CH:41][C:23]=3[F:22])[C:30]3=[CH:31][N:32]=[CH:33][CH:34]=[C:29]3[CH:28]=2)=[O:36])[CH2:47][O:46]1

Participants

9

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11298047(R)-O-((2,2-Dimethyl-1,3-dioxolan-4-yl)methyl)hydroxylamineHCID 68484005HCID 68484005, compound

Product 1

HCID 59452214HCID 59452214, compoundYield 76.3%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

EDCI (259 mg, 1.08 mmol) and HOBt (204 mg, 1.51 mmol) were added to a suspension of sodium 1-(2-fluoro-4-iodo-benzyl)-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (494 mg, 1.08 mmol) in THF (7 ml). The suspension was warmed gently for 1 minute before the addition of a solution of O—((R)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-hydroxylamine (222 mg, 1.51 mmol) in THF (3 ml) followed by DIPEA (0.19 ml, 1.10 mmol). The reaction mixture was stirred at room temperature for 18 hours, poured into ethyl acetate (60 ml) and washed sequentially with 0.1M HCl (10 ml), saturated NaHCO3 solution (10 ml) and brine (10 ml). The organic layer was isolated and dried over magnesium sulphate, then concentrated in vacuo to provide a residue. Trituration of the residue in dichloromethane afforded the title compound as a pale cream solid (0.433 g, 76%). LCMS (method B): RT=2.32 min, (M+H)+=524, M+H+=526.

Workup

  1. washwashed sequentially with 0.1M HCl (10 ml), saturated NaHCO3 solution (10 ml) and brine (10 ml)
  2. customThe organic layer was isolated
  3. dry with materialdried over magnesium sulphate
  4. concentrationconcentrated in vacuo
  5. customto provide a residue

Sources & evidence

ORD record
ord-11b203bb30fd4cecaf5de107ba181c88
Source dataset
uspto-grants-2012_09
Patent number
US08258152B2

Reaction notes

Loading…