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

HRID 564564Notes

Reaction equation

HRID 564564 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].Cl.[Br:35][C:36]1[C:37]([F:44])=[C:38]([CH2:42][NH2:43])[CH:39]=[CH:40][CH:41]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[Br:35][C:36]1[C:37]([F:44])=[C:38]([CH2:42][NH:43][C:26]([C:25]2[CH:29]=[CH:30][CH:31]=[C:23]([C:21]([NH:20][CH2:19][C:10]3[C:11]([NH:12][CH:13]4[CH2:14][CH2:15][O:16][CH2:17][CH2:18]4)=[C:6]4[CH:5]=[N:4][N:3]([CH2:1][CH3:2])[C:7]4=[N:8][C:9]=3[CH2:32][CH3:33])=[O:22])[CH:24]=2)=[O:27])[CH:39]=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 46942196(3-broMo-2-fluorophenyl)MethanaMine hydrochlorideHCID 578132773-[({[1,6-Diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic Acid

Product 1

HCID 57813438N-[(3-Bromo-2-fluorophenyl)methyl]-N'-{[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}-1,3-benzenedicarboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-[({[1,6-diethyl-4-(tetrahydro-2H-pyran-4-ylamino)-1H-pyrazolo[3,4-b]pyridin-5-yl]methyl}amino)carbonyl]benzoic acid (210 mg, 0.466 mmol), [(3-bromo-2-fluorophenyl)methyl]amine hydrochloride (123 mg, 0.513 mmol), HBTU (194 mg, 0.513 mmol) and diisopropyl ethyl amine (0.5 mL) in DCM (10 mL) was stirred at room temperature for about 5 h. It was concentrated, mixed with EtOAc (25 mL), washed with aqueous NaHCO3 (25 mL) and then NH4Cl (25 mL). The organic layer was collected, dried and concentrated to afford the desired product as a crude mixture (330 mg).

Workup

  1. concentrationIt was concentrated
  2. additionmixed with EtOAc (25 mL)
  3. washwashed with aqueous NaHCO3 (25 mL)
  4. customThe organic layer was collected
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e4e4e7e872e24d1e916be6c6477088df
Source dataset
uspto-grants-2011_11
Patent number
US08067408B2

Reaction notes

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