3-[[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methoxy]benzenamine → HCID 67202506, compound

HRID 85182Notes

Reaction equation

HRID 85182 reaction equation
[F:1][CH:2]([F:22])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:13][C:12]2[C:14]([C:19](O)=[O:20])=[CH:15][C:16]([F:18])=[CH:17][C:11]=2[N:10]=1.[CH3:23][C:24]1([CH3:38])[O:28][C@@H:27]([CH2:29][O:30][C:31]2[CH:32]=[C:33]([CH:35]=[CH:36][CH:37]=2)[NH2:34])[CH2:26][O:25]1>>[F:22][CH:2]([F:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([F:18])[CH:15]=[C:14]([C:19]([NH:34][C:33]3[CH:35]=[CH:36][CH:37]=[C:31]([O:30][CH2:29][C@H:27]4[CH2:26][O:25][C:24]([CH3:38])([CH3:23])[O:28]4)[CH:32]=3)=[O:20])[C:12]=2[N:13]=1

Participants

3

Reactant 2

HCID 582789843-[[(4S)-2,2-Dimethyl-1,3-dioxolan-4-yl]methoxy]benzenamineHCID 178524528HCID 178524528, compound

Product 1

HCID 67202506HCID 67202506, compoundYield 48%

Procedure

2-(2-(difluoromethyl)phenyl)-5-fluoro-1H-benzo[d]imidazole-7-carboxylic acid (145; 250 mg, 0.82 mmol) was coupled with (S)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)aniline 146 (prepared as described for 133 in Example 33, steps 1-2, except using (S)-4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane in step 1) as outlined earlier. (S)-2-(2-(Difluoromethyl)phenyl)-N-(3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)phenyl)-6-fluoro-1H-benzo[d]imidazole-4-carboxamide 147 was obtained in 48% yield (200 mg). MS (ESI) calcd for C27H24F3N3O4: 511.17; found: 512 [M+H].

Sources & evidence

ORD record
ord-fbd0fe3c50794f09b910d975f5705850
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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