Ammonia → HCID 49839115, compound

HRID 450137Notes

Reaction equation

HRID 450137 reaction equation
[NH2:1][C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.[Li+].CC([N-]C(C)C)C.Cl[C:17]1[N:22]=[C:21]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:20]=[C:19]([N:29]2[C:33]3[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:32]=3[N:31]=[C:30]2[CH:40]([F:42])[F:41])[N:18]=1.N>C1COCC1.O.C(O)(=O)C>[F:42][CH:40]([F:41])[C:30]1[N:29]([C:19]2[N:20]=[C:21]([N:23]3[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)[N:22]=[C:17]([NH:1][C:2]3[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=3)[N:18]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:32]=2[N:31]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 100093-AminopyridineHCID 2724682Lithium diisopropylamideHCID 534881021-[4-Chloro-6-(morpholin-4-yl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole

Product 1

HCID 49839115HCID 49839115, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-aminopyridine (1.88 g, 20 mmol) in 100 mL THF was added LDA (10 mL, 2 M in THF; 20 mmol) and to the resulting suspension was added 1.99 g (5 mmol) of 1-[4-chloro-6-(4-morpholinyl)-1,3,5-triazin-2-yl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole at room temperature. After 5 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, washed with hot water, and dried. Recrystallization from EtOH (using CH2Cl2 to aid initial solubility) gave 1.65 g (73% yield) of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine: mp 221-223° C.; 1H NMR (CDCl3) δ 8.86 (br, 1H), 8.42 (d, J=2.0 Hz, 1H), 7.99 (d, J=7.8 Hz, 1H), 7.92 (d, J=8.1 Hz, 1H), 7.48 (br t, JHF=53.6 Hz, 1H), 7.35-7.31 (m, 2H), 7.22 (m, exchangeable with D2O, 1H), 6.82 (d, J=8.0 Hz, 1H), 4.04 (s, 3H), 3.92 (m, 4H), 3.81 (m, 4H); Anal. Calcd. for C21H20F2N8O2: C, 55.5; H, 4.4; N, 24.7. Found: C, 55.5; H, 4.4; N, 24.4%.

Workup

  1. customthe precipitate was collected
  2. washwashed with hot water
  3. customdried
  4. customRecrystallization from EtOH (

Sources & evidence

ORD record
ord-d37c47a3f9a148ee8d3d6f2604ded877
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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