Acetic Acid → HCID 57973893, compound

HRID 1864010Notes

Reaction equation

HRID 1864010 reaction equation
[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:30][CH3:31])[C:9]3[C:14]([O:15][CH2:16][C@H:17]4[O:22][CH2:21][CH2:20][NH:19][CH2:18]4)=[CH:13][N:12]=[C:11]([C:23]#[C:24][C:25]([CH3:28])([OH:27])[CH3:26])[C:10]=3[N:29]=2)=[N:4][O:5][N:6]=1.C=O.[C:34](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>CO>[NH2:1][C:2]1[C:3]([C:7]2[N:8]([CH2:30][CH3:31])[C:9]3[C:14]([O:15][CH2:16][C@H:17]4[O:22][CH2:21][CH2:20][N:19]([CH3:34])[CH2:18]4)=[CH:13][N:12]=[C:11]([C:23]#[C:24][C:25]([CH3:26])([OH:27])[CH3:28])[C:10]=3[N:29]=2)=[N:4][O:5][N:6]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 16070095HCID 16070095, compound

Product 1

HCID 57973893HCID 57973893, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 4-(2-(4-amino-1,2,5-oxadiazol-3-yl)-1-ethyl-7-{[(2S)-2-morpholinylmethyl]oxy}-1H-imidazo[4,5-c]pyridin-4-yl)-2-methyl-3-butyn-2-ol (0.13 g, 0.30 mmol) suspended in methanol (2 mL) was added formaldehyde (37% in water, 0.045 mL, 0.6 mmol). After 5 min, acetic acid (0.051 mL, 0.9 mmol) was added following by sodium triacetoxyborohydride (0.16 g, 0.75 mmol). After 1 h. the solvent was removed in vacuo and the residue suspended in 1N NaOH and extracted with ethyl acetate/tetrahydrofuran. The combined organic extracts were washed with brine and dried sodium sulfate. The filtrate was concentrated in vacuo to afford the desired compound as a solid (0.10 g, 77%) MS (ES+) m/z 442 [M+H]+.

Workup

  1. customAfter 1 h. the solvent was removed in vacuo
  2. extractionextracted with ethyl acetate/tetrahydrofuran
  3. washThe combined organic extracts were washed with brine and dried sodium sulfate
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2537eb6089904511af9ea398562ac015
Source dataset
uspto-grants-2009_12
Patent number
US07625890B2

Reaction notes

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