Hydrochloric Acid → HCID 178521261, compound

HRID 730395Notes

Reaction equation

HRID 730395 reaction equation
[CH:1]1([C:7]2[C:8]3[CH:30]=[CH:29][CH:28]=[CH:27][C:9]=3[N:10]([CH2:19][C:20]([CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)=[O:21])[C:11](=[O:18])[N:12]([CH2:14][C:15](O)=[O:16])[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.[NH2:35][C:36]1[CH:37]=[C:38]([C:42]2[NH:43][O:44][C:45](=[O:47])[N:46]=2)[CH:39]=[CH:40][CH:41]=1.Cl.CCN(C(C)C)C(C)C>N1C=CC=CC=1.C(#N)C.CC(OC)(C)C.C1COCC1>[CH:1]1([C:7]2[C:8]3[CH:30]=[CH:29][CH:28]=[CH:27][C:9]=3[N:10]([CH2:19][C:20]([CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)=[O:21])[C:11](=[O:18])[N:12]([CH2:14][C:15]([NH:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([C:42]4[NH:43][O:44][C:45](=[O:47])[N:46]=4)[CH:37]=3)=[O:16])[N:13]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 81531Diisopropylethylamine2×HCID 16733315[5-Cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-benzo[e][1,2,4]triazepin-3-yl]-acetic acidHCID 178507533HCID 178507533, compound

Product 1

HCID 178521261HCID 178521261, compound

Reagents, catalysts & solvents 4

HCID 1049PyridineSolventHCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Preferably, the [5-cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-benzo[e][1,2,4]triazepin-3-yl]-acetic acid is reacted with thionyl chloride in situ, in an organic solvent such as acetonitrile, THF, MTBE, and the like, preferably acetonitrile; and then reacted with 3-(3-amino-phenyl)-2H-[1,2,4]oxadiazol-5-one as its corresponding HCl salt, in the presence of an organic base such as TEA, DIPEA, pyridine, and the like, preferably DIPEA; wherein the base is preferably present in an amount greater than or equal to about 2 equivalents; in the same organic solvent; to yield the 2-[5-cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl )-2-oxo-1,2-dihydro-benzo[e][1,2,4]triazepin-3-yl]-N-[3-(5-oxo-2,5-dihydro-[1,2,4]oxadiazol-3-yl)-phenyl]-acetamide, the compound of formula (Is).

Sources & evidence

ORD record
ord-ee79c8a9aaaa43b8b2529c36994c28bc
Source dataset
uspto-grants-2009_09
Patent number
US07582753B2

Reaction notes

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