1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68513435, compound

HRID 1716595Notes

Reaction equation

HRID 1716595 reaction equation
Cl.[CH3:2][C:3]1[CH:21]=[CH:20][C:6]2[N:7]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:8]([C:10]([OH:13])([CH3:12])[CH3:11])=[N:9][C:5]=2[CH:4]=1.C(N(CC)C(C)C)(C)C.[C:31]([O:35][C:36]([NH:38][C:39]1[CH:40]=[C:41]2[C:45](=[CH:46][CH:47]=1)[CH2:44][CH:43]([C:48](O)=[O:49])[CH2:42]2)=[O:37])([CH3:34])([CH3:33])[CH3:32].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>CN(C=O)C.O>[C:31]([O:35][C:36](=[O:37])[NH:38][C:39]1[CH:40]=[C:41]2[C:45](=[CH:46][CH:47]=1)[CH2:44][CH:43]([C:48]([N:17]1[CH2:16][CH2:15][CH:14]([N:7]3[C:6]4[CH:20]=[CH:21][C:3]([CH3:2])=[CH:4][C:5]=4[N:9]=[C:8]3[C:10]([OH:13])([CH3:12])[CH3:11])[CH2:19][CH2:18]1)=[O:49])[CH2:42]2)([CH3:34])([CH3:32])[CH3:33]

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 68513351HCID 68513351, compoundHCID 68513390HCID 68513390, compound

Product 1

HCID 68513435HCID 68513435, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(5-methyl-1-piperidin-4-yl-1H-benzoimidazol-2-yl)-propan-2-ol hydrochloride salt (158 mg, 0.55 mmol) in DMF (5 ml) was added N,N-diisopropylethylamine (150 mg, 1.15 mmol). After stirring for 10 minutes, 5-tert-butoxycarbonylamino-indan-2-carboxylic acid (140 mg, 0.55 mmol) was added to the reaction mixture followed by EDCI (195 mg, 1.10 mmol) and HOBT (137 mg, 1.10 mmol). After stirring at rt for 4 hours, the reaction mixture was diluted with water, and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with saturated NaHCO3, brine, and dried over Na2SO4. The extracts were filtered and concentrated in vacuo to afford (2-{4-[2-(1-hydroxy-1-methyl-ethyl)-5-methyl-benzoimidazol-1-yl]-piperidine-1-carbonyl}-indan-5-yl)-carbamic acid tert-butyl ester (266 mg, 98%) as a white solid without further purification.

Workup

  1. stirringAfter stirring at rt for 4 hours
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with saturated NaHCO3, brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe extracts were filtered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-408bc26b36fa45cd9e6848e98806bd94
Source dataset
uspto-grants-2010_09
Patent number
US07803816B2

Reaction notes

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