3-Hydroxypropionic acid → N-[[1-(3-hydroxypropanoyl)pyrrolidin-3-yl]methyl]-N-methyl-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide

HRID 589977Notes

Reaction equation

[CH3:1][N:2]([CH2:23][CH:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)[S:3]([N:6]1[C:11]2([CH2:13][CH2:12]2)[CH2:10][N:9]([C:14]2[C:15]3[CH:22]=[CH:21][NH:20][C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:8][CH2:7]1)(=[O:5])=[O:4].CCN(C(C)C)C(C)C.[OH:38][CH2:39][CH2:40][C:41](O)=[O:42].C1CN([P+](Br)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>CS(C)=O>[OH:42][CH2:41][CH2:40][C:39]([N:26]1[CH2:27][CH2:28][CH:24]([CH2:23][N:2]([CH3:1])[S:3]([N:6]2[C:11]3([CH2:13][CH2:12]3)[CH2:10][N:9]([C:14]3[C:15]4[CH:22]=[CH:21][NH:20][C:16]=4[N:17]=[CH:18][N:19]=3)[CH2:8][CH2:7]2)(=[O:4])=[O:5])[CH2:25]1)=[O:38]

Participants

Conditions

Temperature: 40 °C

Procedure

N-methyl-N-(pyrrolidin-3-ylmethyl)-5-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-5,8-diazaspiro[2.5]octane-8-sulfonamide (intermediate 25) (0.042 mmol) was dissolved in dry DMSO (0.5 mL), added DIPEA (0.25 mL), 3-hydroxypropanoic acid (0.050 mmol) and Pybrop (0.050 mmol) then stirred at 40° C. for 1 h. The pure compound was obtained by standard preparative HPLC purification of the reaction mixture.

Workup

customThe pure compound was obtained by standard preparative HPLC purification of the reaction mixture

Sources & evidence

ORD record: ord-bd92120cc44c44c4af45ba052783ba1e
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233964B2

Reaction notes

Loading…