Diisopropylethylamine → 3-{1-[(3-fluoro-2-methyl phenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1909995Notes

Reaction equation

HRID 1909995 reaction equation
Cl.Cl.[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:20]4[C:15](=[N:16][CH:17]=[N:18][C:19]=4[NH2:21])[N:14]([CH3:22])[N:13]=3)=[CH:9][CH:10]=2)[CH2:5][CH2:4]1.[F:23][C:24]1[C:25]([CH3:34])=[C:26]([CH2:30][C:31](O)=[O:32])[CH:27]=[CH:28][CH:29]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[F:23][C:24]1[C:25]([CH3:34])=[C:26]([CH2:30][C:31]([N:3]2[C:11]3[C:6](=[CH:7][C:8]([C:12]4[C:20]5[C:15](=[N:16][CH:17]=[N:18][C:19]=5[NH2:21])[N:14]([CH3:22])[N:13]=4)=[CH:9][CH:10]=3)[CH2:5][CH2:4]2)=[O:32])[CH:27]=[CH:28][CH:29]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 27792472-(3-Fluoro-2-methylphenyl)acetic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 668235503(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 2HCl

Product 1

HCID 534684673-{1-[(3-fluoro-2-methyl phenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 85.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In a 20 mL vial with cap, to the solution of 3-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 2HCl (70 mg, 0.206 mmol), (3-fluoro-2-methylphenyl)acetic acid (34.7 mg, 0.206 mmol), HATU (78 mg, 0.206 mmol) in DMF (2 mL) was added Hunig's base (0.144 mL, 0.825 mmol). The mixture was stirred overnight. The reaction was poured into water, and an off-white solid formed. The solid was filtered to give the title compound (73 mg) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.15 (d, J=1.52 Hz, 3H), 3.24-3.31 (m, 2H), 3.94 (s, 3H), 3.97 (s, 2H), 4.27-4.34 (m, 2H), 7.04-7.11 (m, 2H), 7.19 (d, J=6.32 Hz, 1H), 7.44 (d, J=8.08 Hz, 1H), 7.53 (s, 1H), 8.16 (d, J=8.08 Hz, 1H), 8.25 (s, 1H).

Workup

  1. customan off-white solid formed
  2. filtrationThe solid was filtered

Sources & evidence

ORD record
ord-5b2db607dcb7424caa528804de3d57af
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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