Triethylamine → HCID 59827628, compound

HRID 472058Notes

Reaction equation

HRID 472058 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[CH:12]=[C:13]2[C:19]([CH2:20][CH:21]([CH2:24][CH2:25][CH3:26])[CH2:22][OH:23])=[CH:18][N:17]([C:27]3[CH:32]=[CH:31][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:29][CH:28]=3)[C:14]2=[CH:15][N:16]=1)[CH3:2].CCN(CC)CC.[CH:43]([N:46]=[C:47]=[O:48])([CH3:45])[CH3:44]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH2:9]([C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([CH2:1][CH3:2])[C:4]=1[C:11]1[CH:12]=[C:13]2[C:19]([CH2:20][CH:21]([CH2:24][CH2:25][CH3:26])[CH2:22][O:23][C:47](=[O:48])[NH:46][CH:43]([CH3:45])[CH3:44])=[CH:18][N:17]([C:27]3[CH:28]=[CH:29][C:30]([CH:33]([CH3:35])[CH3:34])=[CH:31][CH:32]=3)[C:14]2=[CH:15][N:16]=1)[CH3:10]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 61277Isopropyl isocyanateHCID 67152539HCID 67152539, compound

Product 1

HCID 59827628HCID 59827628, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-ylmethyl]-pentan-1-ol (100 mg, 0.20 mmol) in DCM (3 mL), DMAP (1 mg), Et3N (60 μL, 0.42 mmol), and isopropyl isocyanate (30 μL, 0.3 mmol) are added, and the mixture is stirred for 18 h at room temperature. All volatiles are removed under reduced pressure, and the product is purified by chromatography on silica gel (EtOAc-hexane, 2:1) to afford isopropyl-carbamic acid 2-[5-(2,6-diethyl-phenyl)-1-(4-isopropyl-phenyl)-1H-pyrrolo[2,3-c]pyridin-3-ylmethyl]-pentyl ester as colorless oil: LCMS m/z 554.18 (2.71 min).

Workup

  1. customAll volatiles are removed under reduced pressure
  2. customthe product is purified by chromatography on silica gel (EtOAc-hexane, 2:1)

Sources & evidence

ORD record
ord-4189c02403ae4a2ea7a64137ca76d2c8
Source dataset
uspto-grants-2014_01
Patent number
US08633193B2

Reaction notes

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