Triethylamine → HCID 51354223, compound

HRID 1879394Notes

Reaction equation

HRID 1879394 reaction equation
CCOP(ON1N=NC2C=CC=CC=2C1=O)(OCC)=O.[C:21]([O:25][C:26]([NH:28][C@@H:29]1[C:39]2[C:34](=[N:35][CH:36]=[CH:37][CH:38]=2)[C@@H:33]([CH2:40][C:41]([OH:43])=O)[CH2:32][CH2:31][C@H:30]1[C:44]1[CH:49]=[CH:48][CH:47]=[C:46]([F:50])[C:45]=1[F:51])=[O:27])([CH3:24])([CH3:23])[CH3:22].[NH:52]1[CH2:57][CH2:56][CH:55]([N:58]2[C:66]3[C:61](=[N:62][CH:63]=[CH:64][CH:65]=3)[NH:60][C:59]2=[O:67])[CH2:54][CH2:53]1.C(N(CC)CC)C>C(OCC)(=O)C.CN(C)C=O>[F:51][C:45]1[C:46]([F:50])=[CH:47][CH:48]=[CH:49][C:44]=1[C@@H:30]1[CH2:31][CH2:32][C@H:33]([CH2:40][C:41](=[O:43])[N:52]2[CH2:53][CH2:54][CH:55]([N:58]3[C:66]4[C:61](=[N:62][CH:63]=[CH:64][CH:65]=4)[NH:60][C:59]3=[O:67])[CH2:56][CH2:57]2)[C:34]2=[N:35][CH:36]=[CH:37][CH:38]=[C:39]2[C@H:29]1[NH:28][C:26](=[O:27])[O:25][C:21]([CH3:24])([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 42939953-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-oneHCID 22293182Bms-973013HCID 58467985HCID 58467985, compound

Product 1

HCID 51354223HCID 51354223, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DEPBT (0.115 g, 0.384 mmol) was added to a dimethylformamide (4 mL) solution of 2-((5S,6S,9R)-5-(tert-butoxycarbonylamino)-6-(2,3-difluorophenyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridin-9-yl)acetic acid (0.111 g, 0.256 mmol), 1-(piperidin-4-yl)-1H-imidazo[4,5-b]pyridin-2(3H)-one (0.084 g, 0.384 mmol) at room temperature. After stirring for 20 min, triethylamine (0.054 mL, 0.384 mmol) was added to the reaction mixture. The reaction was stirred overnight at room temperature. The reaction was diluted with ethyl acetate and washed three times with water. The ethyl acetate layer was separated, dried (sodium sulfate), filtered and concentrated. Flash chromatography using methanol in methylene chloride from 0 to 10% gave the desired product (145 mg, 90%):

Workup

  1. stirringThe reaction was stirred overnight at room temperature
  2. washwashed three times with water
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-7c366ce2c7274bd388884bc1cb18af3a
Source dataset
uspto-grants-2012_11
Patent number
US08314117B2

Reaction notes

Loading…