Morpholine → HCID 86649779, compound

HRID 450187Notes

Reaction equation

HRID 450187 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[C:17]([O:18][CH3:19])[C:12]=3[N:11]=[C:10]2[CH:20]([F:22])[F:21])[N:3]=1.[NH:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1>C1COCC1>[Cl:8][C:6]1[CH:7]=[C:2]([N:23]2[CH2:28][CH2:27][O:26][CH2:25][CH2:24]2)[N:3]=[C:4]([N:9]2[C:13]3[CH:14]=[CH:15][CH:16]=[C:17]([O:18][CH3:19])[C:12]=3[N:11]=[C:10]2[CH:20]([F:22])[F:21])[N:5]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 57419283HCID 57419283, compound

Product 1

HCID 86649779HCID 86649779, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 1-(4,6-dichloro-2-pyrimidinyl)-2-(difluoromethyl)-4-methoxy-1H-benzimidazole (International Publ. No. WO 2005/095389, the disclosure of which is incorporated herein by reference in its entirety) (50 mg, 0.145 mmol) with a ten-fold of excess morpholine in THF at room temperature gave 51 mg (89% yield) of 1-[4-chloro-6-(4-morpholinyl)-2-pyrimidinyl]-2-(difluoromethyl)-4-methoxy-1H-benzimidazole: mp (CH2Cl2/MeOH) 261-263° C.; 1H NMR (CDCl3) δ 7.90 (dd, J=8.4, 0.7 Hz, 1H), 7.47 (t, JHF=53.6 Hz, 1H), 7.37 (t, J=8.2 Hz, 1H), 6.82 (d, J=7.7 Hz, 1H), 6.47 (s, 1H), 4.07 (s, 3H), 3.84 (m, 4H), 3.73 (m, 4H); Anal. Calcd. for C17H16ClF2N5O2: C, 51.6; H, 4.1; N, 17.7. Found: C, 51.7; H, 4.1; N, 17.9%.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-40b1488a8df64cedbe32675161aac553
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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