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Water → 4-[5-[2-(Difluoromethyl)-4-methoxybenzimidazol-1-yl]-3-(1-methylsulfonylpiperidin-4-yl)triazolo[4,5-d]pyrimidin-7-yl]morpholine

HRID 1256579
Notes
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Reaction equation

HRID 1256579 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[F:6][CH:7]([F:40])[C:8]1[N:12]([C:13]2[N:14]=[C:15]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)[C:16]3[N:21]=[N:20][N:19]([CH:22]4[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]4)[C:17]=3[N:18]=2)[C:11]2[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:10]=2[N:9]=1.C([O-])([O-])=O.[K+].[K+].O>C(Cl)Cl>[F:40][CH:7]([F:6])[C:8]1[N:12]([C:13]2[N:14]=[C:15]([N:28]3[CH2:29][CH2:30][O:31][CH2:32][CH2:33]3)[C:16]3[N:21]=[N:20][N:19]([CH:22]4[CH2:23][CH2:24][N:25]([S:2]([CH3:1])(=[O:4])=[O:3])[CH2:26][CH2:27]4)[C:17]=3[N:18]=2)[C:11]2[CH:34]=[CH:35][CH:36]=[C:37]([O:38][CH3:39])[C:10]=2[N:9]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 666981775-[2-(Difluoromethyl)-4-methoxy-1h-benzimidazol-1-yl]-7-(4-morpholinyl)-3-(4-piperidinyl)-3h-[1,2,3]triazolo[4,5-d]pyrimidine

Product 1

HCID 469176544-[5-[2-(Difluoromethyl)-4-methoxybenzimidazol-1-yl]-3-(1-methylsulfonylpiperidin-4-yl)triazolo[4,5-d]pyrimidin-7-yl]morpholine
Yield 87.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methanesulfonyl chloride (0.09 mL, 1.16 mmol) was added dropwise to a mixture of the above amine (107 mg, 0.220 mmol) and powdered K2CO3 (274 mg, 1.98 mmol) in CH2Cl2 (10 mL) at 0° C. The mixture was allowed to warm to room temperature and was stirred for 16.5 hrs. Water was added, the phases were separated, and the aqueous phase was extracted with CH2Cl2 (1×). The combined organic extracts were dried (Na2SO4) and the solvent removed under vacuum. Recrystallization from CH2Cl2/MeOH gave 5-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-3-[1-(methylsulfonyl)-4-piperidinyl]-7-(4-morpholinyl)-3H-[1,2,3]triazolo[4,5-d]pyrimidine (108 mg, 87%): mp 258-259° C.; 1H NMR (CDCl3) δ 7.81 (dd, J=8.4, 0.5 Hz, 1H), 7.41 (t, JHF=53.5 Hz, 1H), 7.39 (t, J=8.2 Hz, 1H), 6.84 (d, J=7.7 Hz, 1H), 4.93 (tt, J=10.5, 4.2 Hz, 1H), 4.79 (br s, 2H), 4.16 (br s, 2H), 4.07 (s, 3H), 4.01-3.90 (m, 6H), 3.14 (m, 2H), 2.89 (s, 3H), 2.60 (m, 2H), 2.35 (m, 2H); Anal. Calcd. for C23H27F2N9O4S: C, 49.0; H, 4.8; N, 22.4. Found: C, 48.9; H, 4.8; N, 22.2%.

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with CH2Cl2 (1×)
  3. dry with materialThe combined organic extracts were dried (Na2SO4)
  4. customthe solvent removed under vacuum
  5. customRecrystallization from CH2Cl2/MeOH

Sources & evidence

ORD record
ord-408758b0833e4340b3739df53ef54e75
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08461158B2

Reaction notes

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