Formaldehyde → HCID 21074209, compound

HRID 1373186Notes

Reaction equation

HRID 1373186 reaction equation
[CH2:1]=O.N[C:4]1[CH:5]=[C:6]([CH:19]=[C:20]([O:22][CH2:23][CH2:24][C:25]2[S:29][CH:28]=[N:27][C:26]=2[CH3:30])[CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][N:11]=1)=[O:8].[C:31]([BH3-])#[N:32].[Na+]>CO>[CH3:1][N:32]([CH3:31])[C:4]1[CH:5]=[C:6]([CH:19]=[C:20]([O:22][CH2:23][CH2:24][C:25]2[S:29][CH:28]=[N:27][C:26]=2[CH3:30])[CH:21]=1)[C:7]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]([OH:18])=[O:17])=[CH:12][N:11]=1)=[O:8]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 58780935HCID 58780935, compound

Product 1

HCID 21074209HCID 21074209, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Formaldehyde (37% wt. in water) (0.021 ml, 0.75 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 solid. The solid was filtered, washed with water, dried and purified on silica gel (5% to 12% MeOH/DCM) to give the title compound as a pale yellow solid (0.020 g, 19%); 1H NMR δ (d6-DMSO): 2.36 (s, 3H), 2.95 (m, 2H), 4.19 (dd, 2H), 6.39 (s, 1H), 6.92 (m, 2H), 6.99 (s, 1H), 8.27 (s, 2H), 8.83 (s, 1H), 8.88 (s, 1H), 11.02 (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 solid
  5. filtrationThe solid was filtered
  6. washwashed with water
  7. customdried
  8. custompurified on silica gel (5% to 12% MeOH/DCM)

Sources & evidence

ORD record
ord-86c4a44b70ff4175be599a6b43b8ace0
Source dataset
uspto-grants-2007_01
Patent number
US07160906B2

Reaction notes

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