Ammonium Chloride → HCID 66576054, compound

HRID 1405251Notes

Reaction equation

F[C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:17]=2)[N:10]=1.[F:27][C:28]1[CH:33]=[C:32]([CH2:34][OH:35])[CH:31]=[CH:30][N:29]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[Cl-].[NH4+]>C1COCC1>[F:8][C:6]1[CH:5]=[CH:4][C:3]([C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH:17]=3)[N:10]=2)=[C:2]([O:35][CH2:34][C:32]2[CH:31]=[CH:30][N:29]=[C:28]([F:27])[CH:33]=2)[CH:7]=1

Participants

Conditions

Temperature: 70 °C

Procedure

To mixture of 4-(2,4-difluorophenyl)-N-{3-[(methylsulfonyl)methyl]phenyl}-1,3,5-triazin-2-amine (75 mg; 0.197 mmol), intermediate 42.1, and 2-fluoro-4-pyridinemethanol (102 mg; 0.781 mmol) in THF (3.5 ml) a 1 M solution of sodium bis(trimethylsilyl)amide in THF (0.391 ml) was added. The batch was stirred under argon for 6 hours at 70° C. After cooling the batch was poored into saturated aqueous ammonium chloride solution. The organic phase was separated, washed with brine, dried (sodium sulfate) and concentrated. The residue was purified by preparative HPLC to give the desired product (38 mg; 0.08 mmol).

Workup

additionwas added
temperatureAfter cooling the batch
customThe organic phase was separated
washwashed with brine
dry with materialdried (sodium sulfate)
concentrationconcentrated
customThe residue was purified by preparative HPLC

Sources & evidence

ORD record: ord-e51f6fba6ab84958a52305e7639793ec
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08916557B2

Reaction notes

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