Pyridine → HCID 67517760, compound

HRID 1465725Notes

Reaction equation

[F:1][C:2]1[CH:57]=[CH:56][CH:55]=[CH:54][C:3]=1[CH2:4][N:5]1[CH:10]2[CH2:11][CH2:12][CH:6]1[CH:7]([C:13]([NH:15][NH:16][C:17]([C:19]1[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=1)[N:24]([C:28]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[N:23]=[C:22]3[C:47]1[CH:52]=[CH:51][N:50]=[C:49]([CH3:53])[CH:48]=1)=O)=[O:14])[CH2:8][CH2:9]2.N1C=CC=CC=1.P(Cl)(Cl)(Cl)=O>C(#N)C>[F:1][C:2]1[CH:57]=[CH:56][CH:55]=[CH:54][C:3]=1[CH2:4][N:5]1[CH:10]2[CH2:11][CH2:12][CH:6]1[CH:7]([C:13]1[O:14][C:17]([C:19]3[CH:20]=[C:21]4[C:25](=[CH:26][CH:27]=3)[N:24]([C:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[N:23]=[C:22]4[C:47]3[CH:52]=[CH:51][N:50]=[C:49]([CH3:53])[CH:48]=3)=[N:16][N:15]=1)[CH2:8][CH2:9]2

Participants

Conditions

Temperature: 100 °C

Procedure

To N′-(8-(2-fluorobenzyl)-8-azabicyclo[3.2.1]octane-2-carbonyl)-3-(2-methylpyridin-4-yl)-1-trityl-1H-indazole-5-carbohydrazide (142 mg, 0.19 mmol) in acetonitrile (1.6 mL) was added pyridine (44 mg, 0.56 mmol), followed by phosphoryl trichloride (86 mg, 0.56 mmol). The reaction mixture was heated at 100° C. under microwave condition for 30 min. After quench with saturated NaHCO3, the mixture was extracted with EtOAc. The combined organic layer was dried and concentrated to give 40 mg crude product. The crude was brought to next step without further purification.

Workup

customAfter quench with saturated NaHCO3
extractionthe mixture was extracted with EtOAc
customThe combined organic layer was dried
concentrationconcentrated

Sources & evidence

ORD record: ord-f1c57f2b6f654d9a83697b98f0acd9ee
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999966B2

Reaction notes

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