Hydrochloric Acid → HCID 178441951, compound

HRID 2168747Notes

Reaction equation

HRID 2168747 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[N:16]=[N:17][C:18]([CH2:36][CH2:37][CH2:38][CH3:39])=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH:28]4[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]4)=[C:23]([C:34]#[N:35])[CH:22]=3)[CH:20]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:40]([Sn](C)(C)C)=[N+:41]=[N-:42].C1(C)C=CC=CC=1.Cl>O>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[N:16]=[N:17][C:18]([CH2:36][CH2:37][CH2:38][CH3:39])=[C:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27][CH:28]4[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33]4)=[C:23]([C:34]4[NH:42][N:41]=[N:40][N:35]=4)[CH:22]=3)[CH:20]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 5104973Azido(trimethyl)stannane2×HCID 673720424-[6-Butyl-5-(3-cyano-4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 178441951HCID 178441951, compoundYield 99.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-[6-butyl-5-(3-cyano-4-cyclohexyloxy-phenyl)-pyridazin-3-yloxy]-piperidine-1-carboxylic acid tert-butyl ester (Example 67, 0.944 mmol, 505 mg), azidotrimethyltin (3.78 mmol, 802 mg, 97%) and toluene (9 mL) was heated at 110° C. for 48 h. More azidotrimethyltin (0.95 mmol, 201 mg, 97%) was added and the reaction mixture was heated at 110° C. for another 24 h. The reaction mixture was stirred with aq. 0.41 N HCl (11.5 mL), diluted with water (30 mL) and extracted with DCM (2×40 mL). The combined DCM extracts were dried over sodium sulfate. Purification by column chromatography on silica gel using 0-7.5% MeOH in DCM gave 4-{6-butyl-5-[4-cyclohexyloxy-3-(1H-tetrazol-5-yl)-phenyl]-pyridazin-3-yloxy}-piperidine-1-carboxylic acid tert-butyl ester as light brown solid (545 mg).

Workup

  1. temperaturethe reaction mixture was heated at 110° C. for another 24 h
  2. extractionextracted with DCM (2×40 mL)
  3. dry with materialThe combined DCM extracts were dried over sodium sulfate
  4. customPurification by column chromatography on silica gel using 0-7.5% MeOH in DCM

Sources & evidence

ORD record
ord-3265fc1b451a4a26b1043839f509690b
Source dataset
uspto-grants-2015_06
Patent number
US09045461B2

Reaction notes

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