1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 46178836, compound

HRID 1890716Notes

Reaction equation

HRID 1890716 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C@:3]21[CH2:42][C:13]1[CH:14]=[C:15]3[C:20](=[CH:21][C:12]=1[CH2:11]2)[N:19]=[CH:18][C:17]([CH2:22][NH:23][C@H:24]([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[CH2:25][CH2:26][NH:27][C:28]1([C:33]([O-:35])=O)[CH2:32][CH2:31][CH2:30][CH2:29]1)=[CH:16]3.[K+].C1C=NC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C=O)C>[O:35]=[C:33]1[C:28]2([CH2:29][CH2:30][CH2:31][CH2:32]2)[NH:27][CH2:26][CH2:25][C@@H:24]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[N:23]1[CH2:22][C:17]1[CH:18]=[N:19][C:20]2[C:15]([CH:16]=1)=[CH:14][C:13]1[CH2:42][C@:3]3([CH2:11][C:12]=1[CH:21]=2)[C:4]1[C:5](=[N:6][CH:7]=[CH:8][CH:9]=1)[NH:10][C:2]3=[O:1]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 181649HOAtHCID 67995839HCID 67995839, compound

Product 1

HCID 46178836HCID 46178836, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of potassium 1-{[(3S)-3-({[(7S)-2′-oxo-1′,2′,6,8-tetrahydrospiro[cyclo-penta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-3-yl]methyl}amino)-3-phenylpropyl]amino}cyclopentanecarboxylate from step B (˜50 mg, ˜0.87 mmol) in DMF (4.5 mL) was added HOAt (18 mg, 0.13 mmol) and EDCI (150 mg, 0.80 mmol, in 4 portions). After 5 hours at ambient temperature, the reaction mixture was placed into a 60° C. bath for 16 hours. After the reaction was allowed to cool back to ambient temperature, the bulk of the DMF was removed in vacuo, before being diluted with chloroform (20 mL) and half-saturated sodium bicarbonate (5 mL). The aqueous layer was separated and extracted once with chloroform. The combined organics were dried over sodium sulfate, filtered and concentrated in vacuo to provide a residue. This residue was applied to a silica gel column for purification, eluting with a gradient of CH2Cl2:MeOH—99:1 to 92:8. Product-containing fractions were pooled and concentrated in vacuo to give the title compound. MS: m/z=544 (M+1). HRMS: m/z=544.2762; calculated m/z=544.2707 for C34H34N5O2.

Workup

  1. customwas placed into a 60° C.
  2. customfor 16 hours
  3. customthe bulk of the DMF was removed in vacuo
  4. additionbefore being diluted with chloroform (20 mL) and half-saturated sodium bicarbonate (5 mL)
  5. customThe aqueous layer was separated
  6. extractionextracted once with chloroform
  7. dry with materialThe combined organics were dried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto provide a residue
  11. customThis residue was applied to a silica gel column for purification
  12. washeluting with a gradient of CH2Cl2
  13. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7f18d0834c3044ccbb2d35245346faad
Source dataset
uspto-grants-2013_08
Patent number
US08507477B2

Reaction notes

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