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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 877774Generated: October 30, 2026

N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide → 4-((3S,4S)-4-methyl-1-(methylsulfonyl)pyrrolidin-3-ylamino)-6-(6-(methylcarbamoyl)pyridin-3-yl)pyrrolo[1,2-b]pyridazine-3-carboxamide

https://huagongshe.com/reaction/877774

Reaction equation

Participants

RoleNameHCIDCharge
ReactantN-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamideHCID 44119560—
Reactant6-bromo-4-((3S,4S)-4-methyl-1-(methylsulfonyl)pyrrolidin-3-ylamino)pyrrolo[1,2-b]pyridazine-3-carboxamideHCID 68291691—
Product4-((3S,4S)-4-methyl-1-(methylsulfonyl)pyrrolidin-3-ylamino)-6-(6-(methylcarbamoyl)pyridin-3-yl)pyrrolo[1,2-b]pyridazine-3-carboxamideHCID 66548111—

Reaction Steps

The title compound was prepared from 6-bromo-4-((3S,4S)-4-methyl-1-(methylsulfonyl)pyrrolidin-3-ylamino)pyrrolo[1,2-b]pyridazine-3-carboxamide using the method previously described in Step 2 of Example 191 and by replacing 2-(4-methoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane with N-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamide. LCMS (method H) retention time=1.09 min. (MH+472.2). 1H NMR (500 MHz, DMSO-d6, appeared as rotomers) δ 11.19 (d, J=7.9 Hz, 1H), 9.11 (d, J=2.0 Hz, 1H), 8.70 (q, J=4.5 Hz, 1H), 8.51 (d, J=1.5 Hz, 1H), 8.41 (dd, J=8.2, 2.2 Hz, 1H), 8.31 (s, 1H), 8.03 (d, J=8.4 Hz, 1H), 7.87 (br. s., 1H), 7.48 (d, J=1.5 Hz, 1H), 7.23 (br. s., 1H), 5.04-4.92 (m, 1H), 3.86-3.63 (m, 2H), 3.38 (d, J=1.5 Hz, 1H), 3.03 (t, J=9.9 Hz, 1H), 2.89 (s, 3H), 2.84 (d, J=5.0 Hz, 3H), 2.72-2.64 (m, 1H), 1.09 (d, J=6.9 Hz, 3H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08987268B2
Source datasetuspto-grants-2015_03
ORD IDord-1b8d6bf3db2c40049863ce84edfffd64
Source noteuspto-grants-2015_03