1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59363380, compound

HRID 906032Notes

Reaction equation

HRID 906032 reaction equation
C[CH2:2][N:3](C(C)C)C(C)C.[CH3:10][Si:11]([CH3:38])([CH3:37])[CH2:12][CH2:13][O:14][CH2:15][N:16]1[C:20]2=[N:21][CH:22]=[C:23]([NH:25][C:26](=[O:36])[NH:27][C@H:28]3[CH2:32][CH2:31][C@H:30]([C:33]([OH:35])=O)[CH2:29]3)[N:24]=[C:19]2[CH:18]=[CH:17]1.Cl.CN.CCN=C=NCCCN(C)C>C(Cl)Cl>[CH3:2][NH:3][C:33]([C@H:30]1[CH2:31][CH2:32][C@H:28]([NH:27][C:26]([NH:25][C:23]2[N:24]=[C:19]3[CH:18]=[CH:17][N:16]([CH2:15][O:14][CH2:13][CH2:12][Si:11]([CH3:38])([CH3:10])[CH3:37])[C:20]3=[N:21][CH:22]=2)=[O:36])[CH2:29]1)=[O:35]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 6364545Methylamine hydrochlorideHCID 67385533HCID 67385533, compound

Product 1

HCID 59363380HCID 59363380, compoundYield 126.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

DIPEA (0.02 mL, 0.11 mmol) was added at RT to a mixture of (1S,3S)-3-{3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-ureido}cyclopentanecarboxylic acid (0.075 g, 0.179 mmol), methylamine hydrochloride (0.024 g, 0.355 mmol), and EDCI (0.051 g, 0.266 mmol) in 1 mL of DCM. The resulting mixture was stirred at RT for 16 hours before being partitioned between H2O and DCM. The aqueous layer was back extracted twice with DCM. The combined organic layers were dried (Na2SO4), filtered, and evaporated. The residue was purified by SiO2 flash chromatography (DCM/MeOH 0 to 10% MeOH) to give 0.06 g of (1S,3S)-3-{3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-ureido}-cyclopentanecarboxylic acid methylamide (76% yield).

Workup

  1. custombefore being partitioned between H2O and DCM
  2. extractionThe aqueous layer was back extracted twice with DCM
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by SiO2 flash chromatography (DCM/MeOH 0 to 10% MeOH)

Sources & evidence

ORD record
ord-edd1dd5014c8484db1b1d8c0799d407b
Source dataset
uspto-grants-2011_09
Patent number
US08012974B2

Reaction notes

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