Oxalyl chloride → HCID 69949079, compound

HRID 2268614Notes

Reaction equation

HRID 2268614 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]([O:11][C:12]([N:14]([C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)[CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([Cl:27])[CH:26]=1)[C:21]([OH:23])=O)=[O:13])([CH3:10])([CH3:9])[CH3:8].CCN(C(C)C)C(C)C.[C:43]1([NH:49][CH2:50][CH2:51][CH2:52][N:53]2[N:57]=[N:56][CH:55]=[N:54]2)[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>ClCCl.CN(C1C=CN=CC=1)C.CN(C=O)C>[C:7]([O:11][C:12](=[O:13])[N:14]([CH2:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([C:21](=[O:23])[N:49]([C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:50][CH2:51][CH2:52][N:53]2[N:57]=[N:56][CH:55]=[N:54]2)[CH:24]=[C:25]([Cl:27])[CH:26]=1)[C:28]1[CH:33]=[CH:32][N:31]=[CH:30][CH:29]=1)([CH3:9])([CH3:8])[CH3:10]

Participants

8

Reactant 4

HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 18348849Benzoic acid,3-chloro-5-[2-[[(1,1-dimethylethoxy)carbonyl]-4-pyridinylamino]ethoxy]-HCID 18349042HCID 18349042, compound

Product 1

HCID 69949079HCID 69949079, compoundYield 25.6%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

2M Oxalyl chloride solution in dichloromethane (0.11 ml), and dry DMF (0.005 ml) were added to a stirred suspension of 3-[2-(tert-butoxycarbonyl-pyridin-4-yl-amino)-ethoxy]-5-chloro-benzoic acid (0.067 g) in dry dichloromethane (1 ml) under nitrogen. After 10 min, DIPEA (0.100 ml) was added followed after a further 40 min by phenyl-(3-tetrazol-2-yl-propyl)-amine (0.033 g) and DMAP (0.004 g). After 7 days the solvent was evaporated and the residue was purified by flash chromatography, eluting with dichloromethane:methanol (98:2 v/v) to give the title compound as a pale yellow oil (0.024 g).

Workup

  1. customAfter 7 days the solvent was evaporated
  2. customthe residue was purified by flash chromatography
  3. washeluting with dichloromethane:methanol (98:2 v/v)

Sources & evidence

ORD record
ord-4bcd220bc03848788401c958f750cf4f
Source dataset
uspto-grants-2001_12
Patent number
US06326386B1

Reaction notes

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