Bicarbonate Ion → [5-({[1-(4-Chloromethyl-benzyl)-1H-[1,2,3]triazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-pyridin-2-yl]-carbamic acid tert-butyl ester

HRID 928416Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([CH2:15][NH:16][C:17]([C:19]2[N:20]=[N:21][N:22]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31]O)=[CH:27][CH:26]=3)[CH:23]=2)=[O:18])=[C:10]([CH3:33])[N:9]=1)([CH3:4])([CH3:3])[CH3:2].S(Cl)([Cl:37])=O.N1C=CC=CC=1.C(=O)(O)[O-]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:34])[NH:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([CH2:15][NH:16][C:17]([C:19]2[N:20]=[N:21][N:22]([CH2:24][C:25]3[CH:30]=[CH:29][C:28]([CH2:31][Cl:37])=[CH:27][CH:26]=3)[CH:23]=2)=[O:18])=[C:10]([CH3:33])[N:9]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of [5-({[1-(4-Hydroxymethyl-benzyl)-1H-[1,2,3]triazole-4-carbonyl]-amino}-methyl)-4,6-dimethyl-pyridin-2-yl]-carbamic acid tert-butyl ester (690 mg, 1.331 mmol) in 10 mL of DCM was added dropwise a solution of thionyl chloride (0.107 mL, 1.464 mmol) and pyridine (1.615 μL, 0.02 mmol) in 10 mL of DCM. The reaction mixture was stirred for 3 h at 40° C. and saturated aqueous bicarbonate solution was added. The layers were separated and the aqueous layer was extracted with DCM. The combined organic solution was dried over MgSO4, filtered and concentrated under vacuum to yield the crude product which was used in the next step without further purification. LCMS (Method A) RtA=1.681; [M+H]+=485.0.

Workup

customThe layers were separated
extractionthe aqueous layer was extracted with DCM
dry with materialThe combined organic solution was dried over MgSO4
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-117bb90845844b69a15d1fe3ff2d2a90
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290485B2

Reaction notes

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