Ammonia → HCID 58102794, compound

HRID 450139Notes

Reaction equation

HRID 450139 reaction equation
[F:1][CH:2]([F:33])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[N:11]=[C:10]([NH:20][C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[N:9]=2)[C:6]2[CH:27]=[CH:28][CH:29]=[C:30]([O:31][CH3:32])[C:5]=2[N:4]=1.[H-].[Na+].I[CH3:37].N>CN(C=O)C.O.C(Cl)Cl.CCOC(C)=O.C(O)(=O)C>[F:33][CH:2]([F:1])[C:3]1[N:7]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][O:17][CH2:18][CH2:19]3)[N:11]=[C:10]([N:20]([CH3:37])[C:21]3[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=3)[N:9]=2)[C:6]2[CH:27]=[CH:28][CH:29]=[C:30]([O:31][CH3:32])[C:5]=2[N:4]=1

Participants

9

Reactant 4

HCID 222AmmoniaHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 49839115HCID 49839115, compound

Product 1

HCID 58102794HCID 58102794, compoundYield 53%

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 21226138Dichloromethane ethylacetateSolvent

Procedure

A solution of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine (0.544 g, 1 mmol) in 15 mL DMF was treated with of NaH and then a slight excess iodomethane was added. After 10 min, the reaction was neutralized with acetic acid and diluted with water. After the pH was made slightly alkaline with aq. NH3, the precipitate was collected and dried. Chromatography on alumina eluting with CH2Cl2/EtOAc (9:1) gave 0.26 g (53% yield) of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-N-methyl-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine: mp (MeOH) 200-201° C.; 1H NMR (DMSO-d6) δ 8.67 (d, J=2.2 Hz, 1H), 8.55 (d, J=4.1 Hz, 1H), 7.89 (ddd, J=8.1, 2.6, 1.5 Hz, 1H), 7.70-7.29 (m, 3H), 6.90 (d, J=8.0 Hz, 1H), 3.94 (s, 3H), 3.84-3.61 (m, 8H), 3.55 (s, 3H); Anal. Calcd. for C22H22F2N8O2: C, 56.4; H, 4.7; N, 23.9. Found: C, 56.5; H, 4.75; N, 24.5%.

Workup

  1. customthe precipitate was collected
  2. customdried

Sources & evidence

ORD record
ord-b48d330dff504ab8b380323cd5adbcbf
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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