Diisopropylethylamine → HCID 66823676, compound

https://huagongshe.com/reaction/1909994

Participants

Role	Name	HCID	Charge
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-Fluoro-3-methylbenzeneacetic acid	HCID 2783145	—
Reactant	Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)	HCID 9886157	—
Reactant	3(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 2HCl	HCID 66823550	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 66823676	HCID 66823676	82.8%

Reaction Steps

In a 20 mL vial with cap, to 3-(2,3-dihydro-1H-indol-5-yl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine 2HCl (70 mg, 0.206 mmol), (2-fluoro-3-methylphenyl)acetic acid (34.7 mg, 0.206 mmol), and 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, off-white solid formed. The solid was filtered to give 3-{1-[(2-fluoro-3-methylphenyl)acetyl]-2,3-dihydro-1H-indol-5-yl}-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (71 mg) as an off-white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.25 (d, J=1.52 Hz, 3H), 3.24-3.32 (m, 2H), 3.92 (s, 2H), 3.94 (s, 3H), 4.30 (t, J=8.46 Hz, 2H), 7.04-7.11 (m, 1H), 7.16 (s, 1H), 7.21 (s, 1H), 7.44 (d, J=8.34 Hz, 1H), 7.53 (s, 1H), 8.16 (d, J=8.34 Hz, 1H), 8.25 (s, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08598156B2
Source dataset	uspto-grants-2013_12
ORD ID	ord-96940240c61340d8834fb43b7bff48ad
Source note	uspto-grants-2013_12