4-Methylmorpholine → 2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-5-cyano-1-(4-benzyloxyphenylcarbamoylmethyl)-benzimidazole

HRID 412546Notes

Reaction equation

HRID 412546 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N:21]([CH2:34][C:35]3[N:39]([CH2:40][C:41](O)=[O:42])[C:38]4[CH:44]=[CH:45][C:46]([C:48]#[N:49])=[CH:47][C:37]=4[N:36]=3)[C:22](=[O:33])[C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].O.ON1C2C=CC=CC=2N=N1.Cl.[CH2:62]([O:69][C:70]1[CH:76]=[CH:75][C:73]([NH2:74])=[CH:72][CH:71]=1)[C:63]1[CH:68]=[CH:67][CH:66]=[CH:65][CH:64]=1.Cl.CN(C)CCCN=C=NCC.CN1CCOCC1>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][C:18]([N:21]([CH2:34][C:35]3[N:39]([CH2:40][C:41](=[O:42])[NH:74][C:73]4[CH:72]=[CH:71][C:70]([O:69][CH2:62][C:63]5[CH:64]=[CH:65][CH:66]=[CH:67][CH:68]=5)=[CH:76][CH:75]=4)[C:38]4[CH:44]=[CH:45][C:46]([C:48]#[N:49])=[CH:47][C:37]=4[N:36]=3)[C:22](=[O:33])[C:23]3[CH:24]=[CH:25][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:27][CH:28]=3)=[CH:19][CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 5

HCID 79724-MethylmorpholineHCID 27238314-Benzyloxyaniline hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 185364772-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonylbenzoyl)aminomethyl]-5-cyanobenzimidazole-1-acetic acid

Product 1

HCID 185365182-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonyl-benzoyl)aminomethyl]-5-cyano-1-(4-benzyloxyphenylcarbamoylmethyl)-benzimidazoleYield 75.3%

Procedure

2-[N-[4-(1-tert-Butoxycarbonylpiperidin-4-yloxy)phenyl]-N-(4-methoxycarbonylbenzoyl)aminomethyl]-5-cyanobenzimidazole-1-acetic acid (632 mg), 1-hydroxybenzotriazole hydrate (128 mg), 4-benzyloxyaniline hydrochloride (223 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (182 mg) and N-methylmorpholine (0.104 ml) were treated in the same manner as in Example 17, Step 10. The solvent was evaporated and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:7-2:8) to give the title compound (605 mg).

Workup

  1. customThe solvent was evaporated
  2. customthe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:7-2:8)

Sources & evidence

ORD record
ord-15560a0139cd4e73b31dafef9908e927
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

Loading…