N,N-Dimethylglycine hydrochloride → 2-(dimethylamino)-1-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)ethanone

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethylglycine hydrochloride	HCID 75605	—
Reactant	1-Hydroxybenzotriazole	HCID 75771	—
Reactant	Diisopropylethylamine	HCID 81531	—
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-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine	HCID 90030300	—
Reactant	3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine	HCID 90030931	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-(dimethylamino)-1-(4-(5-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-2-yl)piperazin-1-yl)ethanone	HCID 118524003	—

Reaction Steps

Using similar reaction conditions as described in step-ii of example-124, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (step 1 compound of example 137) (75 mg, 0.124 mmol) was coupled with 2-(dimethylamino)acetic acid hydrochloride (26 mg, 0.186 mmol) using HATU (71 mg, 0.186 mmol), HOBt (26 mg, 0.186 mmol) and DIPEA (87 μL, 0.498 mmol) in DMF (2 mL) to get 80 mg (93.0%) yield of the title compound. MS: m/z=693.3 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-4cd872bc9f274e5aa38131bf22504d15
Source note	uspto-grants-2016_05