Picolinic acid → HCID 69782915, compound

HRID 1291799Notes

Reaction equation

HRID 1291799 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([OH:9])=[O:8].ClC(N(C)C)=C(C)C.N1C=CC=CC=1.O[C@H:25]([C@@H:47]([NH:55][C:56](=[O:75])[C@H:57]([CH2:71][C:72](=[O:74])[NH2:73])[NH:58][C:59]([C:61]1[CH:70]=[CH:69][C:68]2[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=2)[N:62]=1)=[O:60])[CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[CH2:26][N:27]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[NH:28][C:29](=[O:39])[C@H:30]([CH:36]([CH3:38])[CH3:37])[NH:31][C:32]([O:34][CH3:35])=[O:33]>C(Cl)Cl.O1CCOCC1.CN(C1C=CN=CC=1)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O:9][C@H:25]([C@@H:47]([NH:55][C:56](=[O:75])[C@H:57]([CH2:71][C:72](=[O:74])[NH2:73])[NH:58][C:59]([C:61]1[CH:70]=[CH:69][C:68]2[C:63](=[CH:64][CH:65]=[CH:66][CH:67]=2)[N:62]=1)=[O:60])[CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[CH2:26][N:27]([CH2:40][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[NH:28][C:29](=[O:39])[C@H:30]([CH:36]([CH3:38])[CH3:37])[NH:31][C:32]([O:34][CH3:35])=[O:33])=[O:8]

Participants

8

Reactant 4

HCID 1018Picolinic acidHCID 1049PyridineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 69782440HCID 69782440, compound

Product 1

HCID 69782915HCID 69782915, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

Analogously to Example 108, 51 mg (0.416 mmol) of 2-picolinic acid in 0.8 ml of methylene chloride are converted with 59 μl (0.416 mmol) of 1-chloro-N,N,2-trimethyl-1-propenamine into the acid chloride. After the addition of 0.5 ml of dioxane and 0.4 ml of pyridine to the latter, the mixture is reacted with 148 mg (0.208 mmol) of 1-[2(S)-hydroxy-3(S)-(N-(quinoline-2-carbonyl)-(L)-asparaginyl)amino-4-phenyl-butyl]-1-[phenylmethyl]-2-[N-(methoxycarbonyl)-(L)-valyl]-hydrazine (Example 109) in 5 ml of dioxane in the presence of 0.5 mg of DMAP. Since, after 18 h, not all of the educt has been acylated according to HPLC, further acid chloride is added. Column chromatography (SiO2, methylene chloride→methylene chloride/methanol 15:1) yields the title compound: FAB-MS (M+H)+ +817.

Workup

  1. additionis added

Sources & evidence

ORD record
ord-164e1eae21184955bc66b76706cce03e
Source dataset
uspto-grants-1998_05
Patent number
US05753652

Reaction notes

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