Triethylamine → HCID 11527103, compound

HRID 1664871Notes

Reaction equation

HRID 1664871 reaction equation
C(N(CC)CC)C.[F:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[C@H:16]1[CH2:22][N:21]2[C:23]([CH:26]3[CH2:30][CH2:29][O:28][CH2:27]3)=[CH:24][N:25]=[C:20]2[C@H:19]([NH2:31])[CH2:18][CH2:17]1.Cl[C:33](OC1C=CC([N+]([O-])=O)=CC=1)=[O:34].[Cl-].[Cl-].[O:47]=[C:48]1[NH:56][C:51]2=[NH+:52][CH:53]=[CH:54][CH:55]=[C:50]2[N:49]1[CH:57]1[CH2:62][CH2:61][NH2+:60][CH2:59][CH2:58]1>O1CCCC1.ClCCl>[F:8][C:9]1[C:14]([F:15])=[CH:13][CH:12]=[CH:11][C:10]=1[C@H:16]1[CH2:22][N:21]2[C:23]([CH:26]3[CH2:30][CH2:29][O:28][CH2:27]3)=[CH:24][N:25]=[C:20]2[C@H:19]([NH:31][C:33]([N:60]2[CH2:61][CH2:62][CH:57]([N:49]3[C:50]4[C:51](=[N:52][CH:53]=[CH:54][CH:55]=4)[NH:56][C:48]3=[O:47])[CH2:58][CH2:59]2)=[O:34])[CH2:18][CH2:17]1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 821294-Nitrophenyl chloroformateHCID 67440367HCID 67440367, compoundHCID 178518668HCID 178518668, compound

Product 1

HCID 11527103HCID 11527103, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Triethylamine (43 μL, 0.310 mmol) was added to a solution of the bis hydrochloride salt of (6S,9R)-6-(2,3-difluorophenyl)-3-(tetrahydrofuran-3-yl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-amine (42 mg, 0.103 mmol) and 4-nitrophenyl chloroformate (21 mg, 104 mmol) in tetrahydrofuran (3 mL) at 0° C. After 30 min, 2-oxo-1-piperidinium-4-yl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-4-ium dichloride (45 mg, 0.155 mmol), triethylamine (43 μL, 0.310 mmol) and dichloromethane (3 mL) were added and the mixture allowed to warm to ambient temperature. After 18 h, the reaction was concentrated. Purification by reverse phase HPLC (C-18, 90% water/acetonitrile→100% acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (35 mg). MS 578.2702 (M+1).

Workup

  1. waitAfter 18 h
  2. concentrationthe reaction was concentrated
  3. customPurification by reverse phase HPLC (C-18, 90% water/acetonitrile→100% acetonitrile with 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-36cf92b3bd244bf1ad500405caa02920
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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