Hexamethylenetetramine → 5-((6-(1-(2-Hydroxyethyl)-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde

HRID 876862Notes

Reaction equation

HRID 876862 reaction equation
[N:1]1[N:5]2[CH:6]=[CH:7][C:8]([CH2:10][N:11]3[C:15]4=[N:16][C:17]([C:20]5[CH:21]=[N:22][N:23]([CH2:25][CH2:26][O:27]C6CCCCO6)[CH:24]=5)=[CH:18][N:19]=[C:14]4[N:13]=[N:12]3)=[CH:9][C:4]2=[CH:3][CH:2]=1.C1N2CN3CN(C2)CN1C3.N.O.C[C:47](O)=[O:48].O>>[OH:27][CH2:26][CH2:25][N:23]1[CH:24]=[C:20]([C:17]2[N:16]=[C:15]3[N:11]([CH2:10][C:8]4[CH:7]=[CH:6][N:5]5[N:1]=[CH:2][C:3]([CH:47]=[O:48])=[C:4]5[CH:9]=4)[N:12]=[N:13][C:14]3=[N:19][CH:18]=2)[CH:21]=[N:22]1

Participants

5

Reactant 4

HCID 4101HexamethylenetetramineHCID 12896473Azane;hydrateHCID 21899381Acetic acid--water (1/1)HCID 682894141-(pyrazolo[1,5-a]pyridin-5-ylmethyl)-6-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine

Product 1

HCID 532624195-((6-(1-(2-Hydroxyethyl)-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)pyrazolo[1,5-a]pyridine-3-carbaldehyde

Conditions

Temperature
110 °C

Procedure

To a solution of 1-(pyrazolo[1,5-a]pyridin-5-ylmethyl)-6-(1-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazine 311-a (125 mg, 0.28 mmol) in AcOH/H2O (2 mL/1 mL) was added HMTA (79 mg, 0.56 mmol). The reaction mixture was stirred at 110° C. for 2 h, then treated with NH3.H2O to bring pH to 8. The resulting mixture was then concentrated and purified by prep-TLC to afford the title compound (67 mg). MS (m/z): 389.37 (M+1)+.

Workup

  1. concentrationThe resulting mixture was then concentrated
  2. custompurified by prep-TLC

Sources & evidence

ORD record
ord-1b447263480d4aaf9760678adb8dd986
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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