Methanol → Methanesulfonic Acid

HRID 250774Notes

Reaction equation

HRID 250774 reaction equation
C(N1C2C=C(C=NC)C=CC=2N=C1N)C(C)C.C1(C)C=CC([S:24]([CH:27]([N+]#[C-])C2C=CC(F)=CC=2)(=[O:26])=[O:25])=CC=1.CN.[CH2:40]([N:44]1[C:48]2[CH:49]=[C:50]([C:53]3[N:57]([CH3:58])[CH:56]=[N:55][C:54]=3[C:59]3[CH:64]=[CH:63][C:62]([F:65])=[CH:61][CH:60]=3)[CH:51]=[CH:52][C:47]=2[N:46]=[C:45]1[NH2:66])[CH:41]([CH3:43])[CH3:42].C[OH:68]>>[CH3:27][S:24]([OH:25])(=[O:26])=[O:68].[CH3:27][S:24]([OH:25])(=[O:26])=[O:68].[CH2:40]([N:44]1[C:48]2[CH:49]=[C:50]([C:53]3[N:57]([CH3:58])[CH:56]=[N:55][C:54]=3[C:59]3[CH:60]=[CH:61][C:62]([F:65])=[CH:63][CH:64]=3)[CH:51]=[CH:52][C:47]=2[N:46]=[C:45]1[NH2:66])[CH:41]([CH3:43])[CH3:42]

Participants

7

Reactant 5

HCID 887MethanolHCID 6329MethylamineHCID 10827289a-Tosyl-(4-fluorobenzyl) isocyanideHCID 668688601-Isobutyl-2-amino-6-(methyliminomethyl)-1H-benzimidazoleHCID 668690651-(isobutyl)-2-amino-6-(1-methyl-4 (4-fluorophenyl)-1H-imidazol-5-yl)-1H-benzimidazole

Product 2

HCID 6395Methanesulfonic AcidHCID 866232701-(Isobutyl)-2-amino-6-(1-methyl-4-(4-fluorophenyl)-1H-imidazol-5-yl)-1H-benzimidazole methanesulfonate

Procedure

Beginning with 1-isobutyl-2-amino-6-(methyliminomethyl)-1H-benzimidazole (142 mg, 0.52 mmol), α-(p-toluenesulfonyl)-4-fluorobenzylisocyanide (302 mg, 1.05 mmol), methanol (2.5 ml), and methylamine (1.3 ml, 2M in tetrahydrofuran), 1-(isobutyl)-2-amino-6-(1-methyl-4 (4-fluorophenyl)-1H-imidazol-5-yl)-1H-benzimidazole may be prepared essentially as described in EXAMPLE 72. Treatment with 1 equivalent of methanesulfonic acid provides the title compound (114 mg).

Workup

  1. custommay be prepared essentially

Sources & evidence

ORD record
ord-08c9dd81fecc4ba6a5fb335f5e4dde4d
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

Loading…