Triethylamine → 3-Cyclopropyl-N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]pyridine-2-carboxamide

HRID 1750656Notes

Reaction equation

HRID 1750656 reaction equation
[CH3:1][C@:2]1([NH:21][C:22]2[CH:27]=[N:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][N:23]=2)[CH2:6][CH2:5][CH2:4][C@@H:3]1[NH:7][C:8]([C:10]1[C:15](N2N=CC=N2)=[CH:14][CH:13]=[CH:12][N:11]=1)=[O:9].[CH3:32][C@:33]1(NC2C=NC(C(F)(F)F)=CN=2)[CH2:37]CC[C@@H]1N.C1(C2C(C(O)=O)=NC=CC=2)CC1.C(N(CC)CC)C>>[CH:37]1([C:15]2[C:10]([C:8]([NH:7][C@H:3]3[CH2:4][CH2:5][CH2:6][C@:2]3([CH3:1])[NH:21][C:22]3[CH:27]=[N:26][C:25]([C:28]([F:29])([F:31])[F:30])=[CH:24][N:23]=3)=[O:9])=[N:11][CH:12]=[CH:13][CH:14]=2)[CH2:33][CH2:32]1

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 686851453-Cyclopropylpicolinic acid2×HCID 118308048(1S,2S)-1-Methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine2×HCID 118308152N-[(1S,2S)-2-Methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide

Product 1

HCID 1183081513-Cyclopropyl-N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]pyridine-2-carboxamide

Procedure

Prepared according to the procedure for N-[(1S,2S)-2-methyl-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(2H-1,2,3-triazol-2-yl)pyridine-2-carboxamide (Example 77) from (1S,2S)-1-methyl-1-N-[5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine (Intermediate 25; 48 mg, 0.15 mmol), 3-cyclopropylpyridine-2-carboxylic acid (Intermediate 16; 33 mg, 0.20 mmol) and triethylamine (0.077 ml, 0.55 mmol) except this was purified by column chromatography (silica, 0-50% ethyl acetate/petrol) followed by column chromatography (silica, 0-2.5% methanol/DCM) to afford the title compound.

Workup

  1. customPrepared
  2. customthis was purified by column chromatography (silica, 0-50% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-0530d410de1746dda514ffc54d8a51da
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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