Diisopropylethylamine → (1-cyclopropylmethanesulfonyl-piperidin-3-yl)-{6-methyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyridin-2-yl}-amine

HRID 1916115Notes

Reaction equation

[CH3:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]2[CH2:14][CH2:13][CH2:12][NH:11][CH2:10]2)[C:5]([C:15]2[N:16]=[C:17]3[CH:23]=[CH:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:31])([CH3:30])[CH3:29])[C:18]3=[N:19][CH:20]=2)=[CH:4][CH:3]=1.[CH:32]1([CH2:35][S:36](Cl)(=[O:38])=[O:37])[CH2:34][CH2:33]1.CCN(C(C)C)C(C)C>>[CH:32]1([CH2:35][S:36]([N:11]2[CH2:12][CH2:13][CH2:14][CH:9]([NH:8][C:6]3[C:5]([C:15]4[N:16]=[C:17]5[CH:23]=[CH:22][N:21]([CH2:24][O:25][CH2:26][CH2:27][Si:28]([CH3:30])([CH3:29])[CH3:31])[C:18]5=[N:19][CH:20]=4)=[CH:4][CH:3]=[C:2]([CH3:1])[N:7]=3)[CH2:10]2)(=[O:38])=[O:37])[CH2:34][CH2:33]1

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 14106996Cyclopropylmethanesulphonyl chloride

HCID 69811916{6-methyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyridin-2-yl}-piperidin-3-yl-amine

Product 1

HCID 58177254(1-cyclopropylmethanesulfonyl-piperidin-3-yl)-{6-methyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyridin-2-yl}-amine

Procedure

(1-Cyclopropylmethanesulfonyl-piperidin-3-yl)-{6-methyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyridin-2-yl}-amine was prepared from {6-methyl-3-[5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-pyridin-2-yl}-piperidin-3-yl-amine, and cyclopropyl methanesulfonyl chloride, using 3 equivalents of DIPEA as base and following the general synthetic procedures described in the above Examples.

Sources & evidence

ORD record: ord-fa878ef4c5c04d1786673bbbc177cbee
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618103B2

Reaction notes

Loading…