2,6-Dimethoxybenzoic Acid → 2,6-Dimethoxy-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

HRID 1750601Notes

Reaction equation

HRID 1750601 reaction equation
N1(C2C=CC=CC=2C(N[C@H]2CCC[C@@H]2NC2C=NC(C(F)(F)F)=CN=2)=O)C=CC=N1.Cl.[F:32][C:33]([F:48])([F:47])[C:34]1[N:35]=[CH:36][C:37]([NH:40][C@H:41]2[CH2:45][CH2:44][CH2:43][C@@H:42]2[NH2:46])=[N:38][CH:39]=1.[CH3:49][O:50][C:51]1[CH:59]=[CH:58][CH:57]=[C:56]([O:60][CH3:61])[C:52]=1[C:53](O)=[O:54]>>[CH3:61][O:60][C:56]1[CH:57]=[CH:58][CH:59]=[C:51]([O:50][CH3:49])[C:52]=1[C:53]([NH:46][C@H:42]1[CH2:43][CH2:44][CH2:45][C@@H:41]1[NH:40][C:37]1[CH:36]=[N:35][C:34]([C:33]([F:32])([F:47])[F:48])=[CH:39][N:38]=1)=[O:54]

Participants

4

Reactant 3

HCID 151092,6-Dimethoxybenzoic AcidHCID 118308118(1S,2S)-1-N-[5-(Trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 1183082302-(1H-Pyrazol-1-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Product 1

HCID 1183082452,6-Dimethoxy-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Procedure

Prepared according to the procedure for 2-(1H-pyrazol-1-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide (Example 31) from (1S,2S)-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 14, 213 mg, 0.75 mmol) and 2,6-dimethoxybenzoic acid (CAS number 1466-76-8; 151 mg, 0.83 mmol) except this was then purified by column chromatography (silica, 0-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customPrepared
  2. customthis was then purified by column chromatography (silica, 0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-caab2f306baa4cf18947ce800cdfa587
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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