Sodium Hydroxide → HCID 73504090, compound

HRID 1478560Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@@H:17]4[CH2:22][N:21]([C:23]5[N:28]=[CH:27][C:26]([C:29]6[CH:30]=[N:31][N:32]([CH:34]7[CH2:39][CH2:38][N:37]([C:40](OC(C)(C)C)=O)[CH2:36][CH2:35]7)[CH:33]=6)=[CH:25][N:24]=5)[CH2:20][CH2:19][O:18]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1.[OH-].[Na+]>C=O.C(O)=O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]3[N:13]([CH2:16][C@H:17]4[O:18][CH2:19][CH2:20][N:21]([C:23]5[N:28]=[CH:27][C:26]([C:29]6[CH:30]=[N:31][N:32]([CH:34]7[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][CH2:35]7)[CH:33]=6)=[CH:25][N:24]=5)[CH2:22]4)[N:14]=[N:15][C:10]3=[N:9][CH:8]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

(S)-tert-butyl 4-(4-(2-(2-((6-(1-methyl-1H-pyrazol-4-yl)-1H-[1,2,3]triazolo[4,5-b]pyrazin-1-yl)methyl)morpholino)pyrimidin-5-yl)-1H-pyrazol-1-yl)piperidine-1-carboxylate 550 mg (0.88 mmol) was dissolved in 35% formaldehyde 0.5 ml and formic acid 2.5 ml, and charged with nitrogen, followed by stirring at 90° C. for 18 hours. After the completion of the reaction, the reaction mixture was cooled in an ice bath, and then adjusted to about pH 10 with a NaOH solution, followed by extraction with EA and brine, and the organic layer was dried over MgSO4. Column chromatography (methylene chloride:methanol=10:1) gave a product 161 mg (34%).

Workup

customAfter the completion of the reaction
temperaturethe reaction mixture was cooled in an ice bath
extractionfollowed by extraction with EA and brine
dry with materialthe organic layer was dried over MgSO4

Sources & evidence

ORD record: ord-7d0805449daa4a47b4c9b1408d2f0012
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403831B2

Reaction notes

Loading…