Methanesulfonic Acid → HCID 86649776, compound

HRID 450138Notes

Reaction equation

HRID 450138 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.[CH3:34][S:35]([OH:38])(=[O:37])=[O:36].CCOC(C)=O>CO>[CH3:34][S:35]([OH:38])(=[O:37])=[O:36].[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]([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

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 8857Ethyl AcetateHCID 49839115HCID 49839115, compound

Product 1

HCID 86649776HCID 86649776, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine in MeOH was treated with a slight excess of methanesulfonic acid, to give a clear solution. Addition of EtOAc gave a precipitate, which was collected by filtration and washed with EtOAc. Recrystallization from MeOH/EtOAc gave 4-[2-(difluoromethyl)-4-methoxy-1H-benzimidazol-1-yl]-6-(4-morpholinyl)-N-(3-pyridinyl)-1,3,5-triazin-2-amine methanesulfonate: mp 279-282° C.; 1H NMR (d6-DMSO) δ 10.63 (s, exchangeable with D2O, 1H), 9.19 (s, 1H), 8.55 (d, J=5.5 Hz, 1H), 8.53 (m, 1H), 8.08 (m, 1H), 7.90 (dd, J=8.5, 5.4 Hz, 1H), 7.82 (br t, JHF=53.0 Hz, 1H), 7.43 (t, J=8.2 Hz, 1H), 6.98 (d, J=7.8 Hz, 1H), 4.56 (br m, exchangeable with D20, 1H), 3.99 (s, 3H), 3.86 (m, 4H), 3.75 (m, 4H); Anal. Calcd. for C22H24F2N8O5S: C, 48.0; H, 4.4; N, 20.4. Found: C, 47.8; H, 4.4; N, 20.2%.

Workup

  1. customto give a clear solution
  2. customgave a precipitate, which
  3. filtrationwas collected by filtration
  4. washwashed with EtOAc
  5. customRecrystallization from MeOH/EtOAc

Sources & evidence

ORD record
ord-602210588802499f917466347c7754ad
Source dataset
uspto-grants-2013_07
Patent number
US08486939B2

Reaction notes

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