3-(Pyrimidin-2-yl)pyridine-2-carboxylic acid → N-[(1S,2S)-2-{[3-Cyclopropyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(pyrimidin-2-yl)pyridine-2-carboxamide

HRID 1750702Notes

Reaction equation

HRID 1750702 reaction equation
C(OC1C=NC(C2C=CC=CC=2C(N[C@H]2CCC[C@@H]2NC2C=NC(C(F)(F)F)=CN=2)=O)=NC=1)C.Cl.[CH:36]1([C:39]2[C:40]([NH:49][C@H:50]3[CH2:54][CH2:53][CH2:52][C@@H:51]3[NH2:55])=[N:41][CH:42]=[C:43]([C:45]([F:48])([F:47])[F:46])[N:44]=2)[CH2:38][CH2:37]1.[N:56]1[CH:61]=[CH:60][CH:59]=[N:58][C:57]=1[C:62]1[C:63]([C:68](O)=[O:69])=[N:64][CH:65]=[CH:66][CH:67]=1>>[CH:36]1([C:39]2[C:40]([NH:49][C@H:50]3[CH2:54][CH2:53][CH2:52][C@@H:51]3[NH:55][C:68]([C:63]3[C:62]([C:57]4[N:56]=[CH:61][CH:60]=[CH:59][N:58]=4)=[CH:67][CH:66]=[CH:65][N:64]=3)=[O:69])=[N:41][CH:42]=[C:43]([C:45]([F:47])([F:48])[F:46])[N:44]=2)[CH2:37][CH2:38]1

Participants

4

Reactant 3

HCID 593636623-(Pyrimidin-2-yl)pyridine-2-carboxylic acidHCID 118308108(1S,2S)-1-N-[3-Cyclopropyl-5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride2×HCID 1183081672-(5-Ethoxypyrimidin-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide

Product 1

HCID 118308139N-[(1S,2S)-2-{[3-Cyclopropyl-5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]-3-(pyrimidin-2-yl)pyridine-2-carboxamide

Procedure

Prepared according to the procedure for 2-(5-Ethoxypyrimidin-2-yl)-N-[(1S,2S)-2-{[5-(trifluoromethyl)pyrazin-2-yl]amino}cyclopentyl]benzamide (Example 135) from (1S,2S)-1-N-[3-cyclopropyl-5-(trifluoromethyl)pyrazin-2-yl]cyclopentane-1,2-diamine hydrochloride (Intermediate 48; 105 mg, 0.33 mmol) and 3-(pyrimidin-2-yl)pyridine-2-carboxylic acid (CAS number 1228431-21-7; 79 mg, 0.39 mmol) except after work-up, the organics were loaded directly on to a cation/anion mixed mode cartridge, eluted with DCM, then methanol and 2M ammonia in methanol and concentrated in vacuo. The resulting residue was purified by column chromatography (silica, 0-100% ethyl acetate/petrol) to afford the title compound.

Workup

  1. customPrepared
  2. additionmixed mode cartridge
  3. washeluted with DCM
  4. concentrationmethanol and 2M ammonia in methanol and concentrated in vacuo
  5. customThe resulting residue was purified by column chromatography (silica, 0-100% ethyl acetate/petrol)

Sources & evidence

ORD record
ord-61e35cdc61d7454e90f407e48b1b9f53
Source dataset
uspto-grants-2015_10
Patent number
US09156829B2

Reaction notes

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