2,3-difluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid → HCID 118308198, compound

HRID 1750623Notes

Reaction equation

HRID 1750623 reaction equation
COC1C=CC(C)=CC=1C(N[C@H]1CCC[C@@H]1NC1C=NC(C(F)(F)F)=CN=1)=O.Cl.[F:30][C:31]([F:46])([F:45])[C:32]1[N:33]=[CH:34][C:35]([NH:38][C@H:39]2[CH2:43][CH2:42][CH2:41][C@@H:40]2[NH2:44])=[N:36][CH:37]=1.[F:47][C:48]1[C:56]([F:57])=[CH:55][CH:54]=[C:53]([N:58]2[N:62]=[CH:61][CH:60]=[N:59]2)[C:49]=1[C:50](O)=[O:51]>>[F:47][C:48]1[C:56]([F:57])=[CH:55][CH:54]=[C:53]([N:58]2[N:62]=[CH:61][CH:60]=[N:59]2)[C:49]=1[C:50]([NH:44][C@H:40]1[CH2:41][CH2:42][CH2:43][C@@H:39]1[NH:38][C:35]1[CH:34]=[N:33][C:32]([C:31]([F:30])([F:45])[F:46])=[CH:37][N:36]=1)=[O:51]

Participants

4

Reactant 3

HCID 1177278842,3-difluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid2×HCID 118308118(1S,2S)-1-N-[5-(Trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 1183082742-Methoxy-5-methyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Product 1

HCID 118308198HCID 118308198, compound

Procedure

Prepared according to the procedure for 2-methoxy-5-methyl-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide (Example 37) from (1S,2S)-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 14; 126 mg, 0.45 mmol) and 2,3-difluoro-6-(2H-1,2,3-triazol-2-yl)benzoic acid (Intermediate 39a; 120 mg, 0.535 mmol) except this was purified by column chromatography (silica, 40-100% ethyl acetate/petrol) and then further purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia) to afford the title compound.

Workup

  1. customPrepared
  2. customthis was purified by column chromatography (silica, 40-100% ethyl acetate/petrol)
  3. customfurther purified by reverse phase preparative HPLC (eluted with acetonitrile/water containing 0.1% ammonia)

Sources & evidence

ORD record
ord-37908e380b0b4fc5a6c2547fb50ec18a
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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