Trifluoroacetic acid → (3S)-1-[3-methoxy-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]piperidin-3-amine

HRID 57927Notes

Reaction equation

HRID 57927 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N:25]2[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31]C(=O)OC(C)(C)C)[CH2:26]2)=[N:5][C:6]([N:9]2[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[N:22][CH:21]=[C:20]([CH3:24])[N:19]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[N:10]2)=[CH:7][N:8]=1.FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]1[C:4]([N:25]2[CH2:30][CH2:29][CH2:28][C@H:27]([NH2:31])[CH2:26]2)=[N:5][C:6]([N:9]2[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[N:22][CH:21]=[C:20]([CH3:24])[N:19]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[N:10]2)=[CH:7][N:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86707116tert-butyl N-[(3S)-1-[3-methoxy-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-3-piperidyl]carbamate

Product 1

HCID 72714479(3S)-1-[3-methoxy-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]piperidin-3-amineYield 41%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-butyl N-[(3S)-1-[3-methoxy-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-3-piperidyl]carbamate (75 mg, 0.15 mmol) in dichloromethane 4.0 ml and trifluoroacetic acid (0.80 mL, 10 mmol) was stirred at RT 4 h. The reaction was concentrated and submitted for reverse phase HPLC to give 222 (25 mg) in 41% yield. MS (ESI) m/z: 418.2. 1H NMR (400 MHz, DMSO) δ 9.45 (s, 2H), 9.32 (s, 1H), 8.67 (s, 1H), 8.63 (s, 1H), 8.15 (s, 1H), 4.24 (d, J=10.2 Hz, 1H), 4.06 (d, J=13.3 Hz, 1H), 4.00 (s, 3H), 3.09 (dd, J=24.2, 12.0 Hz, 3H), 2.63 (s, 3H), 1.94 (d, J=15.0 Hz, 2H), 1.76 (d, J=10.0 Hz, 1H), 1.49 (d, J=10.0 Hz, 1H).

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-df54713d415247aeac911e8432321b91
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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