Hydrochloric Acid → (S)-1-(6-(6-Methoxy-6-methyl-1,4-diazepan-1-yl)pyridin-2-yl)-6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 57988Notes

Reaction equation

HRID 57988 reaction equation
[CH3:1][O:2][C@@:3]1([CH3:42])[CH2:9][N:8](C(OC(C)(C)C)=O)[CH2:7][CH2:6][N:5]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N:23]3[C:31]4[CH:30]=[C:29]([C:32]5[CH:33]=[N:34][N:35]([CH2:37][C:38]([F:41])([F:40])[F:39])[CH:36]=5)[N:28]=[CH:27][C:26]=4[CH:25]=[N:24]3)[N:18]=2)[CH2:4]1.Cl>CO>[CH3:1][O:2][C@:3]1([CH3:42])[CH2:4][N:5]([C:17]2[N:18]=[C:19]([N:23]3[C:31]4[CH:30]=[C:29]([C:32]5[CH:33]=[N:34][N:35]([CH2:37][C:38]([F:40])([F:39])[F:41])[CH:36]=5)[N:28]=[CH:27][C:26]=4[CH:25]=[N:24]3)[CH:20]=[CH:21][CH:22]=2)[CH2:6][CH2:7][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86707173(R)-tert-butyl 6-methoxy-6-methyl-4-(6-(6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate

Product 1

HCID 86707172(S)-1-(6-(6-Methoxy-6-methyl-1,4-diazepan-1-yl)pyridin-2-yl)-6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridineYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 6-methoxy-6-methyl-4-(6-(6-(1-(2,2,2-trifluoroethyl)-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepane-1-carboxylate (100 mg, 0.17 mmol) in MeOH (5 mL) was added HCl (conc., 5 mL). The mixture was stirred at room temperature for 4 hours. It was concentrated under reduced pressure. The crude was purified by reverse phase preparative HPLC to afford 261 as a white solid (75 mg, 91%). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.16 (s, 1H), 8.70 (s, 1H), 8.55 (s, 1H), 8.41 (s, 1H), 8.14 (s, 1H), 7.68 (t, 1H), 7.16 (d, 1H), 6.69 (d, 1H), 5.27-5.22 (m, 2H), 4.06-4.03 (m, 2H), 3.67-3.54 (m, 2H), 3.12 (s, 3H), 3.02 (s, 2H), 2.72 (s, 2H), 1.14 (s, 3H); MS (ESI) m/z: 487 [M+H]+.

Workup

  1. concentrationIt was concentrated under reduced pressure
  2. customThe crude was purified by reverse phase preparative HPLC

Sources & evidence

ORD record
ord-b0c0a220b958424bb1054960d94a6da0
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

Loading…