Hydrochloric Acid → HCID 68458293, compound

HRID 2387484Notes

Reaction equation

HRID 2387484 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][C@@H:28]([F:31])[CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:32])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:33].C(OCC)C>C(Cl)Cl>[ClH:33].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20]([CH2:24][CH2:25][N:26]2[CH2:30][CH2:29][C@@H:28]([F:31])[CH2:27]2)[N:19]=[CH:18]3)[C:11](=[O:32])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 25057387HCID 25057387, compound

Product 1

HCID 68458293HCID 68458293, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-4-(benzyloxy)-1-(1-(2-(3-fluoropyrrolidin-1-yl)ethyl)-1H-indazol-5-yl)pyridin-2(1H)-one (10.5 mg, 0.024 mmol) in CH2Cl2 (0.3 mL) was treated with anhydrous HCl in diethyl ether (24 μL, 0.024 mmol, 1.0 M). After stirring at ambient temperature for 2.0 h, the reaction mixture was concentrated, dissolved in CH3CN and H2O, partially concentrated, and then lyophilized to yield the title compound (11.9 mg, quantitative) as an off white solid: 1H NMR (500 MHz, DMSO-d6) δ 10.58 (br s, 0.5H), 8.24 (s, 1H), 7.84 (d, J=9.0 Hz, 1H), 7.79 (s, 1H), 7.60 (d, J=7.5 Hz, 1H), 7.48-7.36 (m, 6H), 6.12 (dd, J=8.0, 3.0 Hz, 1H), 5.99 (d, J=2.5 Hz, 1H), 5.53-5.39 (m, 1H), 5.15 (s, 2H), 4.87 (s, 2H), 3.88-3.51 (m, 5H), 3.21-3.16 (m, 1H), 2.15-2.08 (m, 1H), 1.30-1.23 (m, 1H); ESI MS m/z 433 [M+H]+, HPLC (Method A)>99.0% (AUC), tR=14.1 min.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. dissolutiondissolved in CH3CN
  3. concentrationH2O, partially concentrated

Sources & evidence

ORD record
ord-bb48fbef8f6d4876b10d32570747594c
Source dataset
uspto-grants-2012_09
Patent number
US08268868B2

Reaction notes

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