Ethanol → HCID 178521009, compound

HRID 931223Notes

Reaction equation

[F:1][C:2]([F:12])([F:11])[C:3]1[N:8]=[C:7]([CH:9]=O)[CH:6]=[CH:5][CH:4]=1.Cl.Cl.[NH2:15][C:16]1[CH:17]=[CH:18][C:19]([N:23]2[CH2:28][CH2:27][CH2:26][C@@H:25]([C:29]([N:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[O:30])[CH2:24]2)=[N:20][C:21]=1[NH2:22].S(S([O-])=O)([O-])=O.[Na+].[Na+].C(O)C>O>[N:31]1([C:29]([C@@H:25]2[CH2:26][CH2:27][CH2:28][N:23]([C:19]3[N:20]=[C:21]4[NH:22][C:9]([C:7]5[CH:6]=[CH:5][CH:4]=[C:3]([C:2]([F:12])([F:11])[F:1])[N:8]=5)=[N:15][C:16]4=[CH:17][CH:18]=3)[CH2:24]2)=[O:30])[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

Conditions

Temperature: 110 °C

Procedure

Into a tube was added 6-(trifluoromethyl)picolinaldehyde (150 mg, 0.47 mmol), (R)-(1-(6-amino-5-nitropyridin-2-yl)piperidin-3-yl)(pyrrolidin-1-yl)methanone (Intermediate 1, Step 3) (82.2 mg, 0.47 mmol), sodium dithionite (310.7 mg, 1.78 mmol), ethanol (10 mL) and water (1.5 mL). The vessel was sealed and the reaction mixture was stirred at 110° C. for 16 h. The solvent was evaporated under reduced pressure and water was added to the resulting residue. The mixture was extracted with ethyl acetate, dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified via preparative TLC to afford the title compound (50 mg, 29%) as a yellow solid. MS (ES+APCI) (M+H) 445.2; LCMS retention time 2.657 min (Method G).

Workup

customThe vessel was sealed
customThe solvent was evaporated under reduced pressure and water
additionwas added to the resulting residue
extractionThe mixture was extracted with ethyl acetate
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude material was purified via preparative TLC

Sources & evidence

ORD record: ord-06039163eacd4e4caa0ef925887c43c4
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296745B2

Reaction notes

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