Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1) → (5)-1-(4-(1-methyl-7-(3-methylmorpholino)-1H-pyrazolo-[4,3-d]pyrimidin-5-yl)phenyl)-3-(2-(methylsulfonyl)ethyl)urea

HRID 72191Notes

Reaction equation

HRID 72191 reaction equation
[CH3:1][N:2]1[C:10]2[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]3[CH3:17])=[N:8][C:7]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][CH:28]4[CH2:31]OC4)=[O:26])=[CH:20][CH:19]=3)=[N:6][C:5]=2[CH:4]=[N:3]1.Cl.[CH3:33][S:34](CCN)(=[O:36])=[O:35]>>[CH3:1][N:2]1[C:10]2[C:9]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][C@@H:12]3[CH3:17])=[N:8][C:7]([C:18]3[CH:23]=[CH:22][C:21]([NH:24][C:25]([NH:27][CH2:28][CH2:31][S:34]([CH3:33])(=[O:36])=[O:35])=[O:26])=[CH:20][CH:19]=3)=[N:6][C:5]=2[CH:4]=[N:3]1

Participants

3

Reactant 2

HCID 17749886Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1)HCID 51355347(5)-1-(4-(1-methyl-7-(3-methylmorpholino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-(oxetan-3-yl)urea

Product 1

HCID 51355346(5)-1-(4-(1-methyl-7-(3-methylmorpholino)-1H-pyrazolo-[4,3-d]pyrimidin-5-yl)phenyl)-3-(2-(methylsulfonyl)ethyl)urea

Procedure

This compound was prepared in an analogous fashion to (S)-1-(4-(1-methyl-7-(3-methylmorpholino)-1H-pyrazolo[4,3-d]pyrimidin-5-yl)phenyl)-3-(oxetan-3-yl)urea, using 2-(methylsulfonyl)ethanamine hydrochloride as the starting material. 1H NMR (DMSO-d6, 400 MHz) δ ppm 8.96 (s, 1H), 8.25 (d, J=8.8 Hz, 2H), 8.21 (s, 1H), 7.51 (d, J=8.8 Hz, 2H), 6.42 (t, J=5.9 Hz, 1H), 4.25 to 4.13 (m, 4H), 3.96 to 3.83 (m, 2H), 3.78 to 3.79 (m, 1H), 3.79 to 3.60 (m, 2H), 3.60 to 3.47 (m, 3H), 3.37 to 3.30 (m, 5H), 1.27 (d, J=6.5 Hz, 3H); LC-MS m/z (method C1)=474.2 [M+H]+, RT=3.13 min

Sources & evidence

ORD record
ord-c5cf6b4be41547f787cd5adab110e5ed
Source dataset
uspto-grants-2014_09
Patent number
US08828990B2

Reaction notes

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