Diisopropylethylamine → HCID 67005943, compound

HRID 564581Notes

Reaction equation

HRID 564581 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][C:15]2[CH:16]=[C:17]([C:21]3[C:26]([F:27])=[CH:25][CH:24]=[C:23]([CH2:28][NH:29][C:30]([C:32]4[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=4)[C:35](O)=[O:36])=[O:31])[CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH2:10][C@@H:9]1[CH3:41])=[O:7])([CH3:4])[CH3:3].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:66][CH2:67][C:68]1[C:73]([CH2:74][CH3:75])=[N:72][C:71]2[N:76]([CH2:79][CH3:80])[N:77]=[CH:78][C:70]=2[C:69]=1[NH:81][CH:82]1[CH2:87][CH2:86][O:85][CH2:84][CH2:83]1.CCN(C(C)C)C(C)C>ClCCl>[CH2:79]([N:76]1[C:71]2=[N:72][C:73]([CH2:74][CH3:75])=[C:68]([CH2:67][NH:66][C:35]([C:34]3[CH:33]=[C:32]([C:30]([NH:29][CH2:28][C:23]4[CH:24]=[CH:25][C:26]([F:27])=[C:21]([C:17]5[CH:18]=[CH:19][CH:20]=[C:15]([CH2:14][N:11]6[CH2:12][CH2:13][N:8]([C:6]([O:5][C:2]([CH3:3])([CH3:1])[CH3:4])=[O:7])[C@@H:9]([CH3:41])[CH2:10]6)[CH:16]=5)[CH:22]=4)=[O:31])[CH:40]=[CH:39][CH:38]=3)=[O:36])[C:69]([NH:81][CH:82]3[CH2:83][CH2:84][O:85][CH2:86][CH2:87]3)=[C:70]2[CH:78]=[N:77]1)[CH3:80]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 57813489HCID 57813489, compoundHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Product 1

HCID 67005943HCID 67005943, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

205(a) 3-{[({3′-[((3S)-4-{[(1,1-Dimethylethyl)oxy]carbonyl}-3-methyl-1-piperazinyl)methyl]-6-fluoro-3-biphenylyl}methyl)amino]carbonyl}benzoic acid (1150 mg, 2.0 mmol) was dissolved in dichloromethane (DCM) (100 mL), and then HBTU (830 mg, 2.2 mmol), 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (620 mg, 2.0 mmol), and DIPEA (1.4 mL, 8.0 mmol) were added. The mixture was allowed to stir under argon at room temperature overnight. Solvents were concentrated and then purified on a 40 g Redi-Sep cartridge and eluting with 0.5% MeOH in DCM. Collected clean fractions were combined solvent concentrated to give 1,1-dimethylethyl (2S)-4-[(5′-{[({3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]phenyl}carbonyl)amino]methyl}-2′-fluoro-3-biphenylyl)methyl]-2-methyl-1-piperazinecarboxylate (1.15 g, 66.5%) as a white solid.

Workup

  1. concentrationSolvents were concentrated
  2. custompurified on a 40 g Redi-Sep cartridge
  3. washeluting with 0.5% MeOH in DCM
  4. customCollected clean fractions
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9f8364b5079c4fdeb84648e02bd97eb5
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

Loading…