1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 71764073, compound

HRID 1644783Notes

Reaction equation

HRID 1644783 reaction equation
[C:1]([O:9][CH2:10][C@H:11]([C:36]1[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[C:38]([C:46]([F:49])([F:48])[F:47])[CH:37]=1)[O:12][C@H:13]1[CH2:21][CH2:20][C@H:19]2[C@@H:15]([CH2:16][N:17]([C:22]([NH:24][C:25](=[O:28])[CH2:26]Cl)=[O:23])[CH2:18]2)[C@@H:14]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1>C1COCC1>[C:1]([O:9][CH2:10][C@H:11]([C:36]1[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[C:38]([C:46]([F:49])([F:48])[F:47])[CH:37]=1)[O:12][C@H:13]1[CH2:21][CH2:20][C@H:19]2[C@@H:15]([CH2:16][N:17]([C:22]3[O:23][CH2:26][C:25](=[O:28])[N:24]=3)[CH2:18]2)[C@@H:14]1[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH3:35])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 71764072HCID 71764072, compound

Product 1

HCID 71764073HCID 71764073, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the intermediate from Step C (8.84 g, 12.43 mmol) in THF (600 mL) and DBU (3.75 mL, 24.86 mmol) was heated at 50° C. for 2.5 hr. The volatiles were removed, and the crude material was purified by column chromatography [(6% methanol/EtOAc)/EtOAC 0 to 66% for 2900 mL, then 66% to 80% for 1200 mL] to give the title compound. M++1: 613.60.

Workup

  1. customThe volatiles were removed
  2. customthe crude material was purified by column chromatography [(6% methanol/EtOAc)/EtOAC 0 to 66% for 2900 mL

Sources & evidence

ORD record
ord-b66a0863362a481ea90e89d537188ece
Source dataset
uspto-grants-2012_02
Patent number
US08124633B2

Reaction notes

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