Hydrochloric Acid → HCID 178423508, compound

HRID 80866Notes

Reaction equation

[F:1][CH:2]([F:44])[C:3]1[C:7](C=O)=[C:6]([N:10]2[CH2:42][CH2:41][C:13]3[N:14]=[C:15]([C:20]4[C:28]([CH3:29])=[CH:27][CH:26]=[C:25]5[C:21]=4[C:22]([CH3:40])=[N:23][N:24]5S(C4C=CC(C)=CC=4)(=O)=O)[N:16]=[C:17]([O:18]C)[C:12]=3[CH2:11]2)[N:5]([CH3:43])[N:4]=1.Cl.C(=O)(O)[O-].[Na+]>C(O)C>[F:44][CH:2]([F:1])[C:3]1[CH:7]=[C:6]([N:10]2[CH2:42][CH2:41][C:13]3[N:14]=[C:15]([C:20]4[C:28]([CH3:29])=[CH:27][CH:26]=[C:25]5[C:21]=4[C:22]([CH3:40])=[N:23][NH:24]5)[N:16]=[C:17]([OH:18])[C:12]=3[CH2:11]2)[N:5]([CH3:43])[N:4]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 3-(difluoromethyl)-5-(2-(3,5-dimethyl-1-tosyl-1H-indazol-4-yl)-4-methoxy-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-1-methyl-1H-pyrazole-4-carbaldehyde (0.8 g, 1.287 mmol) in ethanol (10.7 mL) was added concentrated HCl (2.1 mL). The microwave vessel was sealed and the mixture was irradiated at 125° C. for 1 h 20 min. The reaction mixture was then cooled to 0° C. and poured into ice water. Solid sodium bicarbonate was slowly added to neutralize the reaction mixture to pH=7, then the crude product was extracted with DCM (3×) and the combined organic layers were dried over sodium sulfate to provide 6-(3-(difluoromethyl)-1-methyl-1H-pyrazol-5-yl)-2-(3,5-dimethyl-1H-indazol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ol, MS (ESI+) m/z 426.4 (M+H)+.

Workup

customThe microwave vessel was sealed
customthe mixture was irradiated at 125° C. for 1 h 20 min
extractionthe crude product was extracted with DCM (3×)
dry with materialthe combined organic layers were dried over sodium sulfate

Sources & evidence

ORD record: ord-6309c73fd9e54dc1973a0e05031a5a4e
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846656B2

Reaction notes

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