Dimethylformamide → 6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carbonyl chloride

HRID 588150Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=O)[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:4]=2[CH:3]=1.CN(C=O)C.C(Cl)(=O)C([Cl:43])=O>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([Cl:43])=[O:10])[C:5]2[C:11]([O:33][CH3:34])=[N:12][N:13]([C:14]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

6-chloro-3-methoxy-1-trityl-1H-pyrazolo[4,3-c]pyridine-4-carboxylic acid (Intermediate 36B, 440 mg, 0.936 mmol) was taken up in DCM (9.32 ml). DMF (93 n1) was added and the reaction was cooled to 0° C. Oxalyl chloride (164 μl, 1.873 mmol) was added and the mixture was allowed to stir for 1 hr eventually reaching room temperature. The mixture was concentrated in vacuo and then further dried under high vacuum. The residue was carried forward without further purification. MS: [M+H]+ m/z 484 (Methyl ester formed LCMS, sample prepared in MeOH).

Workup

customeventually reaching room temperature
concentrationThe mixture was concentrated in vacuo
customfurther dried under high vacuum
customThe residue was carried forward without further purification
customMS: [M+H]+ m/z 484 (Methyl ester formed LCMS, sample prepared in MeOH)

Sources & evidence

ORD record: ord-ee7edfcbcb374fee91fe209306952d87
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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