HCID 11327446, compound → HCID 11361452, compound

HRID 1160107Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([S:8][CH2:9][C:10]([NH:12][C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=2[NH2:23])=O)[C:5]([C:24]#[N:25])=[C:4]([S:26][CH3:27])[N:3]=1>CC(O)=O>[NH2:1][C:2]1[N:3]=[C:4]([S:26][CH3:27])[C:5]([C:24]#[N:25])=[C:6]([S:8][CH2:9][C:10]2[NH:12][C:13]3[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=3[N:23]=2)[N:7]=1

Participants

Conditions

Temperature: 120 °C

Procedure

To a 10 mL recovery flask was added 2-(2-amino-5-cyano-6-methylsulfanyl-pyrimidin-4-ylsulfanyl)-N-(2-amino-5-trifluoromethyl-phenyl)-acetamide (and regioisomer) (10 mg, 0.0241 mmol) and AcOH (2 mL). The solution was stirred at 120° C. for 1 h. The reaction mixture was concentrated. The resulting film was resuspended in 1:1 CH3CN/H2O and lyophilized to give 2-amino-4-methylsulfanyl-6-(6-trifluoromethyl-1H-benzoimidazol-2-ylmethylsulfanyl)-pyrimidine-5-carbonitrile as a tan powder (9 mg, 94%). LC/MSD (HP Series 1100 MSD) Expected MW: 396.04, Observed M+H, 397.0, Retention time: 1.49. Analytical LC: 98%, Retention time: 4.46 (11 minute run). 1H-NMR, DMSO-d6, Varian 400 MHz δ 12.69 (m, 1H), 8.10 (bs, 1H), 7.91-7.79 (d, 1H), 7.76-7.64 (dd, 1H), 7.51-7.46 (dd, 1H), 4.68 (s, 2H) ppm.

Workup

concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record: ord-4e4fdd762f304713919d7979c74132f8
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07816353B2

Reaction notes

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