Glyoxal → HCID 178510411, compound

HRID 1428041Notes

Reaction equation

HRID 1428041 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[NH2:8][CH2:9][C:10]([N:12]1[CH2:17][CH2:16][CH:15]([C:18]2[CH:23]=[CH:22][C:21]([NH:24][C:25]([C:27]3[NH:28][CH:29]=[C:30]([C:32]#[N:33])[N:31]=3)=[O:26])=[C:20]([C:34]3[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=3)[CH:19]=2)[CH2:14][CH2:13]1)=[O:11].[BH-](OC(C)=O)(OC(C)=O)[O:41][C:42]([CH3:44])=O.[Na+].C(C=O)=O>C(Cl)Cl>[C:3]([OH:5])([C:2]([F:7])([F:6])[F:1])=[O:4].[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:34]1([C:20]2[CH:19]=[C:18]([CH:15]3[CH2:16][CH2:17][N:12]([C:10](=[O:11])[CH2:9][NH:8][CH2:44][CH2:42][OH:41])[CH2:13][CH2:14]3)[CH:23]=[CH:22][C:21]=2[NH:24][C:25]([C:27]2[NH:28][CH:29]=[C:30]([C:32]#[N:33])[N:31]=2)=[O:26])[CH2:39][CH2:38][CH2:37][CH2:36][CH:35]=1

Participants

6

Reactant 3

HCID 7860GlyoxalHCID 5049666Sodium triacetoxyborohydrideHCID 178510410HCID 178510410, compound

Product 2

HCID 6422Trifluoroacetic acidYield 0.1%HCID 178510411HCID 178510411, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4-cyano-1H-imidazole-2-carboxylic acid {4-[1-(2-amino-acetyl)-piperidin-4-yl]-2-cyclohex-1-enyl-phenyl]-amide trifluoroacetic acid salt (as prepared in the previous step, 0.42 g, 0.77 mmol) in CH2Cl2 (20 mL) was treated with Na(OAc)3BH (0.33 g, 1.54 mmol) and solid glyoxal (44.6 mg, 0.77 mmol). The mixture stirred at room temperature for 1 h, and the solvent was evaporated in vacuo. The residue was taken up in MeOH and the solids filtered off, and the filtrate was concentrated in vacuo. Reverse phase HPLC (C-18 column) (20% to 60% acetonitrile in water with 0.1% TFA over 30 min) afforded the title compound (83 mg, 19% over two steps) as a white solid. 1H-NMR (CD3OD; 400 MHz): δ 8.16-8.09 (m, 1H), 8.05-8.01 (m, 1H), 7.22-7.15 (m, 1H), 7.11-7.06 (m, 1H), 5.84-5.79 (m, 1H), 4.72-4.62 (m, 1H), 4.24-3.91 (m, 2H), 3.89-3.80 (m, 2H), 3.28-3.18 (m, 2H), 2.92-2.79 (m, 2H), 2.28 (br s, 4H), 1.98-1.89 (m, 2H), 1.89-1.76 (m, 4H), 1.76-1.57 (m, 2H). LC-MS (ESI, m/z): Calcd. for C26H32N6O3 477.2 (M+H). found 477.2.

Workup

  1. customthe solvent was evaporated in vacuo
  2. filtrationthe solids filtered off
  3. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3b7356cbaeb24b4e9f7c0dacad74abb4
Source dataset
uspto-grants-2015_01
Patent number
US08933091B2

Reaction notes

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