Hydrochloric Acid → HCID 178521261, compound

HRID 730394Notes

Reaction equation

HRID 730394 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](Cl)=[O:16])[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[NH2:31][C:32]1[CH:33]=[C:34]([C:38]2[NH:39][O:40][C:41](=[O:43])[N:42]=2)[CH:35]=[CH:36][CH:37]=1.Cl.CCN(C(C)C)C(C)C>C(#N)C.CC(OC)(C)C.C1COCC1.C1(C)C=CC=CC=1.N1C=CC=CC=1>[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]([NH:31][C:32]3[CH:37]=[CH:36][CH:35]=[C:34]([C:38]4[NH:39][O:40][C:41](=[O:43])[N:42]=4)[CH:33]=3)=[O:16])[N:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

10

Reactant 4

HCID 313Hydrochloric AcidHCID 81531Diisopropylethylamine2×HCID 57834911[5-Cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-benzo[e][1,2,4]triazepin-3-yl]-acetyl chlorideHCID 178507533HCID 178507533, compound2×

Product 1

HCID 178521261HCID 178521261, compound

Reagents, catalysts & solvents 5

HCID 1049PyridineSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

The [5-cyclohexyl-1-(2-cyclopentyl-2-oxo-ethyl)-2-oxo-1,2-dihydro-benzo[e][1,2,4]triazepin-3-yl]-acetyl chloride is reacted with 3-(3-amino-phenyl)-2H-[1,2,4]oxadiazol-5-one, a known compound or compound prepared by known methods, wherein the 3-(3-amino-phenyl)-2H-[1,2,4]oxadiazol-5-one may be present as a free base or, for example, 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 from about 1 to about 2 equivalents; in an aprotic organic solvent such as acetonitrile, toluene, THF, MTBE, and the like, preferably acetonitrile; 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).

Workup

  1. customa known compound or compound prepared

Sources & evidence

ORD record
ord-b285390890404985abbb497ef051c03d
Source dataset
uspto-grants-2009_09
Patent number
US07582753B2

Reaction notes

Loading…