Trifluoroacetic acid → 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-{[6-(piperazin-1-ylmethyl)pyridin-2-yl]amino}pyridine-2-carbonitrile

HRID 1504871Notes

Reaction equation

HRID 1504871 reaction equation
C(OC([NH:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[CH:17]=[C:18]([NH:24][C:25]2[N:30]=[C:29]([CH2:31][N:32]3[CH2:37][CH2:36][N:35](C(OC(C)(C)C)=O)[CH2:34][CH2:33]3)[CH:28]=[CH:27][CH:26]=2)[C:19]([C:22]#[N:23])=[N:20][CH:21]=1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C@H:9]1[CH2:14][CH2:13][CH2:12][CH2:11][C@H:10]1[NH:15][C:16]1[CH:17]=[C:18]([NH:24][C:25]2[CH:26]=[CH:27][CH:28]=[C:29]([CH2:31][N:32]3[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]3)[N:30]=2)[C:19]([C:22]#[N:23])=[N:20][CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86731739tert-butyl 4-[(6-{[5-({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclohexyl}amino)-2-cyanopyridin-3-yl]amino}pyridin-2-yl)methyl]piperazine-1-carboxylate

Product 1

HCID 867317405-{[(1R,2S)-2-aminocyclohexyl]amino}-3-{[6-(piperazin-1-ylmethyl)pyridin-2-yl]amino}pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-[(6-{[5-({(1R,2S)-2-[(tert-butoxycarbonyl)amino]cyclohexyl}amino)-2-cyanopyridin-3-yl]amino}pyridin-2-yl)methyl]piperazine-1-carboxylate (90 mg, 0.15 mmol) in dichloromethane (1.5 mL) was added trifluoroacetic acid (0.17 mL, 2.2 mmol) and the reaction mixture was stirred for 1 hour at room temperature. The reaction was then concentrated under reduced pressure to afford 5-{[(1R,2S)-2-aminocyclohexyl]amino}-3-{[6-(piperazin-1-ylmethyl)pyridin-2-yl]amino}pyridine-2-carbonitrile. The material was used in the next step without further purification. MS ESI calc'd for C22H31N8 [M+H]+ 407. found 407.

Workup

  1. concentrationThe reaction was then concentrated under reduced pressure

Sources & evidence

ORD record
ord-2ea29a686cea4c7bbc158d25ddabe59c
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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