Sodium hydride → HCID 73388519, compound

HRID 523053Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]([OH:26])([CH3:25])[CH2:5][N:6]1[CH:10]=[C:9]([C:11]2[CH:12]=[CH:13][C:14]3[CH:19]=[N:18][C:17](S(C)(=O)=O)=[N:16][C:15]=3[N:24]=2)[CH:8]=[N:7]1.[CH3:27][N:28]1[C:32]([C:33]2[CH:38]=[CH:37][C:36]([NH:39]C=O)=[C:35]([O:42][CH3:43])[CH:34]=2)=[CH:31][N:30]=[C:29]1[CH3:44]>CN1C(=O)CCC1.C1COCC1>[CH3:27][N:28]1[C:32]([C:33]2[CH:38]=[CH:37][C:36]([NH:39][C:17]3[N:18]=[CH:19][C:14]4[CH:13]=[CH:12][C:11]([C:9]5[CH:8]=[N:7][N:6]([CH2:5][C:4]([CH3:25])([OH:26])[CH3:3])[CH:10]=5)=[N:24][C:15]=4[N:16]=3)=[C:35]([O:42][CH3:43])[CH:34]=2)=[CH:31][N:30]=[C:29]1[CH3:44]

Participants

Conditions

Temperature: 160 °C

Procedure

A suspension of NaH (4.3 mg), 2-methyl-1-(4-(2-(methylsulfonyl)pyrido[2,3-d]pyrimidin-7-yl)-1H-pyrazol-1-yl)propan-2-ol (Preparation 69, 15.5 mg, 0.045 mmol), N-(4-(1,2-dimethyl-1H-imidazol-5-yl)-2-methoxyphenyl)formamide (Preparation 74, 16.4 mg, 0.067 mmol) in NMP/THF (1/3 mL) was stirred at 160° C. under microwave irradiation for 2 hours. The reaction mixture was filtered, diluted with NaCl solution and extracted with EtOAc. The EtOAc portion was purified by elution through an SCX-2 column using 2M NH3/MeOH to give the title compound as yellow oil (3 mg, 14%).

Workup

filtrationThe reaction mixture was filtered
additiondiluted with NaCl solution
extractionextracted with EtOAc
customThe EtOAc portion was purified by elution through an SCX-2 column

Sources & evidence

ORD record: ord-44057c07e57c47a7baee29f5621d2b30
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09334286B2

Reaction notes

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