Diisopropylethylamine → N-[(3-Bromo-4-fluorophenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}pentanediamide

HRID 657385Notes

Reaction equation

HRID 657385 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][C:11](=[O:18])[CH2:12][CH2:13][CH2:14][C:15]([OH:17])=O)[CH:5]=[CH:6][C:7]=1[F:8].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:43][CH2:44][C:45]1[C:50]([CH2:51][CH3:52])=[N:49][C:48]2[N:53]([CH2:56][CH3:57])[N:54]=[CH:55][C:47]=2[C:46]=1[NH:58][CH:59]1[CH2:64][CH2:63][O:62][CH2:61][CH2:60]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl.C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH2:9][NH:10][C:11](=[O:18])[CH2:12][CH2:13][CH2:14][C:15]([NH:43][CH2:44][C:45]2[C:46]([NH:58][CH:59]3[CH2:60][CH2:61][O:62][CH2:63][CH2:64]3)=[C:47]3[CH:55]=[N:54][N:53]([CH2:56][CH3:57])[C:48]3=[N:49][C:50]=2[CH2:51][CH3:52])=[O:17])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 578198715-{[(3-bromo-4-fluorophenyl)methyl]amino}-5-oxopentanoic AcidHCID 596832145-(Aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine

Product 1

HCID 57819876N-[(3-Bromo-4-fluorophenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}pentanediamideYield 112.5%

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A mixture of 5-{[(3-bromo-4-fluorophenyl)methyl]amino}-5-oxopentanoic acid (920 mg, 2.89 mmol), HBTU (1130 mg, 2.98 mmol), 5-(aminomethyl)-1,6-diethyl-N-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-b]pyridin-4-amine (820 mg, 2.71 mmol) and diisopropyl ethyl amine (1 mL) in DCM/THF (1:1, 100 mL) was stirred at room temperature overnight. The mixture was concentrated, mixed with EtOAc (50 mL) and washed by NaHCO3 (50 mL) and NH4Cl (50 mL). The organic parts were collected, dried and concentrated to afford the desired product (1.84 g).

Workup

  1. concentrationThe mixture was concentrated
  2. additionmixed with EtOAc (50 mL)
  3. washwashed by NaHCO3 (50 mL) and NH4Cl (50 mL)
  4. customThe organic parts were collected
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-707727b27b7e444090057df593cd72cc
Source dataset
uspto-grants-2011_12
Patent number
US08071588B2

Reaction notes

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