Water → HCID 178484281, compound

HRID 1053643Notes

Reaction equation

HRID 1053643 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11](C1CCCCO1)[N:10]=[C:9]2[CH2:21][N:22]([CH3:34])[CH2:23][CH2:24][N:25](C)[C:26](=O)OC(C)(C)C.O.CC#N.[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42]>ClCCl>[F:39][C:40]([F:45])([F:44])[C:41]([OH:43])=[O:42].[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][N:10]=[C:9]2[CH2:21][N:22]([CH3:34])[CH2:23][CH2:24][NH:25][CH3:26]

Participants

6

Reactant 4

HCID 962WaterHCID 6342Acetonitrile2×HCID 6422Trifluoroacetic acid2×HCID 117608698HCID 117608698, compound

Product 1

HCID 178484281HCID 178484281, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R/S) tert-butyl N-[2-([[5-(2-methoxyethoxy)-1-(oxan-2-yl)-1H-indazol-3-yl]methyl](methyl)amino)ethyl]-N-methylcarbamate (156 mg, 0.33 mmol, 1.00 equiv) in trifluoroacetic acid (3 mL) and dichloromethane (2 mL) was stirred at room temperature for 4 h. The reaction mixture was concentrated under vacuum and the crude product was purified by Prep-HPLC with the following conditions: Column, XBridge Shield RP 18, 5 m, 19×150 mm; mobile phase, water with 50 mmol CF3COOH and CH3CN (10.0% CH3CN up to 28.0% in 2 min, up to 46.0% in 10 min, up to 100.0% in 1 min, down to 10.0% in 1 min); Detector, UV 254 nm to give 122.3 mg (70%) of N1-((5-(2-methoxyethoxy)-1H-indazol-3-yl)methyl)-N1,N2-dimethylethane-1,2-diamine trifluoroacetate as a colorless oil. 1H-NMR (300 MHz, D2O): δ 7.54 (d, J=9.0 Hz, 1H), 7.22 (d, J=1.8 Hz, 1H), 7.16 (dd, J=9.0 Hz, 2.1 Hz, 1H), 4.78-4.72 (m, 2H), 4.20-4.13 (m, 2H), 3.80-3.74 (m, 2H), 3.60-3.42 (m, 4H), 3.36 (s, 3H), 2.89 (s, 3H), 2.70 (s, 3H) ppm. LCMS (method M, ESI): RT=1.00 min, m/z=293.0 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe crude product was purified by Prep-HPLC with the following conditions
  3. waitup to 100.0% in 1 min
  4. waitdown to 10.0% in 1 min)

Sources & evidence

ORD record
ord-689a1c7731d845e8b3afe4ea43149862
Source dataset
uspto-grants-2016_07
Patent number
US09394258B2

Reaction notes

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