Hydrochloric Acid → HCID 86707150, compound

HRID 57968Notes

Reaction equation

HRID 57968 reaction equation
[OH:1][C@@:2]1([CH3:41])[CH2:8][N:7](C(OC(C)(C)C)=O)[CH2:6][CH2:5][N:4]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]3[C:30]4[CH:29]=[C:28]([C:31]5[CH:32]=[N:33][N:34]([CH2:36][C:37]([F:40])([F:39])[F:38])[CH:35]=5)[N:27]=[CH:26][C:25]=4[CH:24]=[N:23]3)[N:17]=2)[CH2:3]1.Cl>CO>[CH3:41][C@@:2]1([OH:1])[CH2:3][N:4]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N:22]3[C:30]4[CH:29]=[C:28]([C:31]5[CH:32]=[N:33][N:34]([CH2:36][C:37]([F:40])([F:39])[F:38])[CH:35]=5)[N:27]=[CH:26][C:25]=4[CH:24]=[N:23]3)[N:17]=2)[CH2:5][CH2:6][NH:7][CH2:8]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86707151HCID 86707151, compound

Product 1

HCID 86707150HCID 86707150, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (R)-tert-butyl 6-hydroxy-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 (46 mg, 0.08 mmol) in MeOH (3 mL) was added HCl solution (conc. 3.0 mL) and stirred at room temperature for 4 hours. The mixture was concentrated under reduced pressure. The crude was purified by reverse phase preparative HPLC to afford 248 as a white solid (36 mg, 94%). 1H NMR (500 MHz, DMSO-d6) δ (ppm) 9.16 (s, 1H), 8.77 (s, 1H), 8.54 (s, 1H), 8.50 (s, 1H), 8.25 (s, 1H), 7.67 (t, 1H), 7.12 (d, 1H), 6.72 (d, 1H), 5.25-5.20 (t, 2H), 4.68 (s, 1H), 4.03-4.00 (m, 2H), 3.57-3.48 (m, 2H), 3.08-3.06 (m, 2H), 2.72 (d, 1H), 2.60 (d, 1H), 1.14 (s, 3H); MS (ESI) m/z: 473 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-0220c5f0750e41898fa45c84e6a5ad7c
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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