2-Methylbenzaldehyde → HCID 58780951, compound

HRID 1373187Notes

Reaction equation

HRID 1373187 reaction equation
[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=O.[NH2:10][C:11]1[CH:12]=[C:13]([CH:26]=[C:27]([O:29][CH2:30][CH2:31][C:32]2[S:36][CH:35]=[N:34][C:33]=2[CH3:37])[CH:28]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][N:18]=1)=[O:15].C([BH3-])#N.[Na+]>CO>[CH3:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][NH:10][C:11]1[CH:12]=[C:13]([CH:26]=[C:27]([O:29][CH2:30][CH2:31][C:32]2[S:36][CH:35]=[N:34][C:33]=2[CH3:37])[CH:28]=1)[C:14]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:25])=[O:24])=[CH:19][N:18]=1)=[O:15]

Participants

5

Reactant 3

HCID 107222-MethylbenzaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58780935HCID 58780935, compound

Product 1

HCID 58780951HCID 58780951, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Methylbenzaldehyde (0.035 ml, 0.3 mM) was added to a solution of 2-[3-amino-5-(4-methyl-thiazol-5-yl) ethoxy benzoyl]amino-5-pyridine carboxylic acid (0.10 g 0.25 mM) and 4A molecular sieves (0.25 g) in methanol (15 ml), under an inert atmosphere at room temperature. After 1 hr sodium cyanoborohydride (0.019 g, 0.3 mM) was added and the reaction mixture stirred for 40 hrs. The reaction mixture was filtered, concentrated in vacuo, 2M NaOH added to pH=11–12 then acidified with 2M HCl to precipitate a colourless solid. The solid was filtered, washed with water to give the title compound as a colourless solid (0.12 g, 96%); 1H NMR δ (d6-DMSO): 2.33 (m, 6H), 3.19 (dd, 2H), 4.13 (dd, 2H), 4.26 (s, 2H), 6.33 (s, 1H), 6.83 (s, 1H), 6.90 (s, 1H), 7.09–7.19 (m, 3H), 7.26 (s, 1H), 8.28 (s, 2H), 8.83 (s, 1H), 8.88 (s, 1H), 10.87 (s, 1H), 13.09 (bs, 1H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated in vacuo, 2M NaOH
  3. additionadded to pH=11–12
  4. customto precipitate a colourless solid
  5. filtrationThe solid was filtered
  6. washwashed with water

Sources & evidence

ORD record
ord-e8c4fb89dc7e4b51980d33a6e4e838ec
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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