Pyridine → HCID 66635554, compound

HRID 510069Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:4]=1[CH2:5][NH:6][C:7]1[C:12]([NH2:13])=[CH:11][N:10]=[C:9]([C:14]2[C:22]3[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=3)[N:16]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[F:31])[N:15]=2)[N:8]=1.[S:38](N)(N)(=[O:40])=[O:39].N1C=CC=CC=1>ClCCl>[CH3:1][O:2][C:3]1[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:4]=1[CH2:5][N:6]1[C:7]2[N:8]=[C:9]([C:14]3[C:22]4[C:17](=[N:18][CH:19]=[C:20]([F:23])[CH:21]=4)[N:16]([CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=4[F:31])[N:15]=3)[N:10]=[CH:11][C:12]=2[NH:13][S:38]1(=[O:40])=[O:39]

Participants

Conditions

Temperature: 160 °C

Procedure

550 mg (1.093 mmol) of the compound from example 92A were divided between 11 microwave vessels. 50 mg of the substance in each were admixed with 48 mg (0.496 mmol) of sulfamide and 2.5 ml of pyridine and then heated at 160° C. under microwave radiation for 30 min. Subsequently, all batches were combined and freed of the solvent under reduced pressure. The residue was taken up in dichloromethane and extracted three times with water. The phases were separated and the organic phase was dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was then purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). This gave 0.130 g (12% of theory, purity 50%) of the title compound.

Workup

extractionextracted three times with water
customThe phases were separated
dry with materialthe organic phase was dried with sodium sulfate
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was then purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record: ord-0bf5ac7f67f44938a149355ffc6439a6
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09096592B2

Reaction notes

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