Bis-(1H-imidazol-2-YL)-methanone → HCID 118036298, compound

HRID 1777980Notes

Reaction equation

HRID 1777980 reaction equation
[C:1](C1NC=CN=1)(C1NC=CN=1)=[O:2].[C:13]([C:15]1[C:16]([O:45][C@H:46]([CH3:50])[CH2:47][O:48][CH3:49])=[CH:17][C:18]([NH:21][C:22]([N:24]2[C:33]3[C:28](=[CH:29][C:30]([CH2:39][NH:40][C@@H:41]([CH3:44])[CH2:42][OH:43])=[C:31]([CH:34]([O:37][CH3:38])[O:35][CH3:36])[N:32]=3)[CH2:27][CH2:26][CH2:25]2)=[O:23])=[N:19][CH:20]=1)#[N:14]>C(Cl)Cl>[C:13]([C:15]1[C:16]([O:45][C@H:46]([CH3:50])[CH2:47][O:48][CH3:49])=[CH:17][C:18]([NH:21][C:22]([N:24]2[C:33]3[C:28](=[CH:29][C:30]([CH2:39][N:40]4[C@@H:41]([CH3:44])[CH2:42][O:43][C:1]4=[O:2])=[C:31]([CH:34]([O:35][CH3:36])[O:37][CH3:38])[N:32]=3)[CH2:27][CH2:26][CH2:25]2)=[O:23])=[N:19][CH:20]=1)#[N:14]

Participants

4

Reactant 2

HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 118037111HCID 118037111, compound2×

Product 1

HCID 118036298HCID 118036298, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of carbonyl diimidazole (49 mg, 0.301 mmol) and N-(5-cyano-4-(((R)-1-methoxypropan-2-yl)oxy)pyridin-2-yl)-7-(dimethoxymethyl)-6-((((S)-1-hydroxypropan-2-yl)amino)methyl)-3,4-dihydro-1,8-naphthyridine-1(2H)-carboxamide (intermediate 148, 118 mg, 0.223 mmol) in DCM (10 ml) was heated in a septum sealed vial at 45° C. for 2.5 h. The cooled reaction mixture was partitioned between DCM and aqueous citric acid solution (5% w/w), extracted 2× with DCM, the DCM layers dried over Na2SO4 and evaporated to give the title compound as a yellow-white solid. (UPLC-MS 6) tR 1.14; ESI-MS 555.3 [M+H]+.

Workup

  1. temperaturewas heated in a septum
  2. customsealed vial at 45° C. for 2.5 h
  3. customThe cooled reaction mixture
  4. customwas partitioned between DCM and aqueous citric acid solution (5% w/w)
  5. extractionextracted 2× with DCM
  6. dry with materialthe DCM layers dried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-2330a27f231341d1bee96d16bea46c3b
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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