Triethylamine → N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-{[6-fluoro-3'-(hydroxymethyl)-3-biphenylyl]methyl}-1,3-benzenedicarboxamide

HRID 564487Notes

Reaction equation

HRID 564487 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:32][CH3:33])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=3)[C:26](O)=[O:27])=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:58][CH2:59][C:60]1[CH:61]=[CH:62][C:63]([F:74])=[C:64]([C:66]2[CH:71]=[CH:70][CH:69]=[C:68]([CH2:72][OH:73])[CH:67]=2)[CH:65]=1.C(N(CC)CC)C>C(Cl)Cl>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH2:32][CH3:33])=[C:10]([CH2:19][NH:20][C:21]([C:23]3[CH:31]=[CH:30][CH:29]=[C:25]([C:26]([NH:58][CH2:59][C:60]4[CH:65]=[C:64]([C:66]5[CH:71]=[CH:70][CH:69]=[C:68]([CH2:72][OH:73])[CH:67]=5)[C:63]([F:74])=[CH:62][CH:61]=4)=[O:27])[CH:24]=3)=[O:22])[C:11]([NH:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 578132773-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic AcidHCID 57813296[5'-(Aminomethyl)-2'-fluoro-3-biphenylyl]methanol

Product 1

HCID 57813265N-{[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-N'-{[6-fluoro-3'-(hydroxymethyl)-3-biphenylyl]methyl}-1,3-benzenedicarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-amino)carbonyl]benzoic acid (0.045 g, 0.1 mmol) in CH2Cl2 (2 mL) was stirred under argon at room temperature. HBTU (0.038 g, 0.1 mmol) was added followed by [5′-(aminomethyl)-2′-fluoro-3-biphenylyl]methanol (0.0231 g, 0.1 mmol) and triethylamine (28 μL, 0.2 mmol). The resulting mixture was stirred for three days. The solvents were pumped off and the residue was purified on the CombiFlash (12 g silica gel column) eluted with 70-100% EtOAc/hexane) to afford the title compound. LC-MS m/z 664.8 (M+H)+, 1.75 min (ret time).

Workup

  1. customthe residue was purified on the CombiFlash (12 g silica gel column)
  2. washeluted with 70-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-ee5233de4acb43088df09de463b127f5
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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