Water → HCID 59176424, compound

HRID 628672Notes

Reaction equation

HRID 628672 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7](=[O:50])[CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[CH:18]=[CH:19][N:20]=[C:21]([CH2:22][N:23]([C@@H:40]4[C:49]5[N:48]=[CH:47][CH:46]=[CH:45][C:44]=5[CH2:43][CH2:42][CH2:41]4)[CH2:24][CH2:25][CH2:26][N:27]4[CH2:32][CH2:31][N:30](C(OC(C)(C)C)=O)[CH2:29][CH2:28]4)[C:10]2=3)[CH2:3][CH2:2]1.FC(F)(F)C(O)=O.[OH-].[Na+].O>ClCCl>[O:1]1[CH2:6][CH2:5][N:4]([C:7](=[O:50])[CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[C:11]3[CH:18]=[CH:19][N:20]=[C:21]([CH2:22][N:23]([CH2:24][CH2:25][CH2:26][N:27]4[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]4)[C@@H:40]4[C:49]5[N:48]=[CH:47][CH:46]=[CH:45][C:44]=5[CH2:43][CH2:42][CH2:41]4)[C:10]2=3)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 59176489HCID 59176489, compound

Product 1

HCID 59176424HCID 59176424, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.50 mmol of (S)-tert-butyl 4-(3-(((9-(2-morpholino-2-oxoethyl)-9H-pyrido[3,4-b]indol-1-yl)methyl)(5,6,7,8-tetrahydroquinolin-8-yl)amino)propyl)piperazine-1-carboxylate was dissolved in 2 ml of dichloromethane and treated with 2 ml of trifluoroacetic acid. After the reaction was stirred at ambient temperature for 2 hours it was cooled to 0° C. with ice bath and then neutralized with 1M NaOH solution carefully. Let the mixture warmed up to room temperature. The organic layer was separated, dried over magnesium sulfate, filtered off, and evaporated. The desired product was purified with column chromatography using dichloromethane:methanol:NH4OH (9:1:0.1). ESI+ MS: m/z (rel intensity) 582.3 (100, [M+H]+). 1H-NMR (400 MHz, CDCl3): δ 8.31 (d, 1H, J=5.6 Hz), 8.28 (d, 1H, J=4.8 Hz), 8.11 (d, 1H, J=9.2 Hz), 7.89 (d, 1H, J=5.2 Hz), 7.57 (t, 1H, J=6.8 Hz), 7.32-7.25 (m, 5H), 6.94 (dt, 1H, J=2.8, 4.8 Hz), 5.67 (d, 1H, J=16.4 Hz), 4.37 (s, 2H), 4.14 (t, 1H, J=9.2 Hz), 4.05 (d, 1H, J=16.8 Hz), 3.93 (d, 1H, J=14.8 Hz), 3.83-3.76 (m, 1H), 3.72-3.47 (m, 4H), 3.45-3.30 (m, 1H), 3.29-3.26 (m, 1H), 2.88-2.51 (m, 6H), 2.41-2.32 (m, 2H), 2.11-2.02 (m, 2H), 1.90-1.59 (m, 8H), 1.02-0.96 (m, 1H), 0.95-0.80 (m, 1H). Elemental Analysis (C/H/N): C34H43N2O2×0.95 mol H2O; Calculated: 68.19/7.56/16.37. Found: 68.18/7.38/16.23.

Workup

  1. temperaturewas cooled to 0° C. with ice bath
  2. temperaturewarmed up to room temperature
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered off
  6. customevaporated
  7. customThe desired product was purified with column chromatography

Sources & evidence

ORD record
ord-9be7788601a34d3c95488f39de88d833
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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