Pyrrolidine → rac-(1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-[3-hydroxy-1-(pyrrolidine-1-carbonyl)-propyl]-[1,4]diazepan-5-one)

HRID 2095535Notes

Reaction equation

HRID 2095535 reaction equation
COC(=O)C(N1C(=O)CC[N:11]([C:16](=O)/[CH:17]=[CH:18]/[C:19]2C=CC(Cl)=C(Cl)C=2)CC1)CCO.[Cl:29][C:30]1[CH:31]=[C:32](/[CH:37]=[CH:38]/[C:39]([N:41]2[CH2:47][CH2:46][C:45](=[O:48])[N:44]([CH:49]3[CH2:53][CH2:52][O:51][C:50]3=[O:54])[CH2:43][CH2:42]2)=[O:40])[CH:33]=[CH:34][C:35]=1[Cl:36].N1CCCC1>CCO>[Cl:29][C:30]1[CH:31]=[C:32](/[CH:37]=[CH:38]/[C:39]([N:41]2[CH2:47][CH2:46][C:45](=[O:48])[N:44]([CH:49]([C:50]([N:11]3[CH2:16][CH2:17][CH2:18][CH2:19]3)=[O:54])[CH2:53][CH2:52][OH:51])[CH2:43][CH2:42]2)=[O:40])[CH:33]=[CH:34][C:35]=1[Cl:36]

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 670742441-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-4-(2-oxo-tetrahydro-furan-3-yl)-[1,4]diazepan-5-one2×HCID 67074795(rac)-2-{4-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-4-hydroxy-butyric acid methyl ester

Product 1

HCID 58232104rac-(1-[(E)-3-(3,4-Dichloro-phenyl)-acryloyl]-4-[3-hydroxy-1-(pyrrolidine-1-carbonyl)-propyl]-[1,4]diazepan-5-one)Yield 88%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In analogy to the procedure described in example 3, treatment of (rac)-2-{4-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-7-oxo-[1,4]diazepan-1-yl}-4-hydroxy-butyric acid methyl ester (with 50% of the lactone, 1-[(E)-3-(3,4-dichloro-phenyl)-acryloyl]-4-(2-oxo-tetrahydro-furan-3-yl)-[1,4]diazepan-5-one) (intermediate 6) in EtOH with pyrrolidine over night at RT gave 88% of the titled compound as white foam. MS: 468.1 (MH+, 2Cl).

Sources & evidence

ORD record
ord-9206a6b2b36a4af29c2fbf685c0971ee
Source dataset
uspto-grants-2013_05
Patent number
US08445674B2

Reaction notes

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