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1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 86695180, compound

HRID 1504024
Notes
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Reaction equation

HRID 1504024 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:16]2[C:17]3[C:18]4[CH2:19][C@H:20]([CH2:29][C:30]([OH:32])=O)[CH2:21][CH2:22][C:23]=4[S:24][C:25]=3[N:26]=[CH:27][N:28]=2)[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH4+].[Cl-].CC[N:37]=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.CN(C)C1C=CN=CC=1>[C:30]([CH2:29][C@H:20]1[CH2:19][C:18]2[C:17]3[C:16]([O:15][CH:12]4[CH2:11][CH2:10][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH2:14][CH2:13]4)=[N:28][CH:27]=[N:26][C:25]=3[S:24][C:23]=2[CH2:22][CH2:21]1)(=[O:32])[NH2:37]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 25517Ammonium ChlorideHCID 757711-HydroxybenzotriazoleHCID 86695179HCID 86695179, compound

Product 1

HCID 86695180HCID 86695180, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 14284
4-(Dimethylamino)pyridine
Catalyst
HCID 6228DimethylformamideSolvent

Procedure

To a 50-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen and containing a solution of 2-[(12R)-3-[(4-[[(tert-butoxy)carbonyl]amino]cyclohexyl)oxy]-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1-(9),2(7),3,5-tetraen-12-yl]acetic acid (98 mg, 0.21 mmol, 1.00 equiv) in 4 mL of DMF was added NH4Cl (68 mg, 1.27 mmol, 6.00 equiv), EDCI (61 mg, 0.32 mmol, 1.50 equiv), 4-dimethylaminopyridine (39 mg, 0.32 mmol, 1.50 equiv) and HOBt (43 mg, 0.32 mmol, 1.50 equiv) successively. The resulting solution was stirred overnight at room temperature and quenched with water and extracted with 3×50 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (2:1) to give tert-butyl N-(4-[[(12R)-12-(carbamoylmethyl)-8-thia-4,6-diazatricyclo[7.4.0.0[2,7]]trideca-1(9),2(7),3,5-tetraen-3-yl]oxy]cyclohexyl)carbamate (72 mg, 74%) as a white solid.

Workup

  1. customTo a 50-mL round-bottom flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customquenched with water
  4. extractionextracted with 3×50 mL of ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-08a2859f5e6c4047a87e8db69dbc5ce7
Source dataset
uspto-grants-2015_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09212190B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes