Potassium Hydroxide → HCID 71240443, compound

HRID 80836Notes

Reaction equation

HRID 80836 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:51])=[C:8]([N:10]2[CH2:50][CH2:49][C:13]3[N:14]=[C:15]([C:29]4[CH:37]=[CH:36][CH:35]=[C:34]5[C:30]=4[C:31]([CH3:48])=[CH:32][N:33]5S(C4C=CC(C)=CC=4)(=O)=O)[N:16]=[C:17]([N:18]4[CH2:23][CH2:22][N:21]([CH2:24][C:25]([NH2:27])=[O:26])[CH2:20][C@H:19]4[CH3:28])[C:12]=3[CH2:11]2)[CH:9]=1)([CH3:3])[CH3:2].[OH-].[NH4+].[OH-].[K+]>C(O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:51])=[C:8]([N:10]2[CH2:50][CH2:49][C:13]3[N:14]=[C:15]([C:29]4[CH:37]=[CH:36][CH:35]=[C:34]5[C:30]=4[C:31]([CH3:48])=[CH:32][NH:33]5)[N:16]=[C:17]([N:18]4[CH2:23][CH2:22][N:21]([CH2:24][C:25]([NH2:27])=[O:26])[CH2:20][C@H:19]4[CH3:28])[C:12]=3[CH2:11]2)[CH:9]=1)([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 14923Ammonium HydroxideHCID 71240492(R)-2-(4-(6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)acetamide

Product 1

HCID 71240443HCID 71240443, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (R)-2-(4-(6-(5-isopropyl-2-methylphenyl)-2-(3-methyl-1-tosyl-1H-indol-4-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-yl)-3-methylpiperazin-1-yl)acetamide (0.075 mg, 0.106 mmol), 30% ammonium hydroxide (0.63 mL 15.94 mmol) and potassium hydroxide (0.054 g, 0.956 mmol) in ethanol (3 mL) was heated in a microwave reactor at 100° C. for 1 h. The reaction mixture was concentrated and then filtered before being purified via HPLC (RP C18, 15-85% CH3CN in H2O with 0.1% NH4OH to provide the title compound. 1H NMR (400 MHz, CD3CN) δ ppm 9.16 (br. s., 1 H) 7.45 (d, J=8.08 Hz, 1H) 7.25 (dd, J=7.20, 1.14 Hz, 1 H) 7.15 (dd, J=15.28, 7.71 Hz, 2 H) 7.01-7.09 (m, 2 H) 6.82-6.94 (m, 2 H) 5.80 (br. s., 1 H) 3.94-4.13 (m, 3 H) 3.51-3.60 (m, 1 H) 3.41-3.50 (m, 1 H) 3.28-3.41 (m, 2 H) 2.95-3.12 (m, 2 H) 2.82-2.95 (m, 3 H) 2.78 (d, J=10.86 Hz, 1 H) 2.57-2.66 (m, 1 H) 2.47-2.56 (m, 1 H) 2.37 (td, J=10.74, 3.03 Hz, 1 H) 2.26 (s, 3 H) 2.05 (s, 3 H) 1.30 (d, J=6.82 Hz, 3 H) 1.23 (dd, J=6.82, 1.01 Hz, 6 H); MS (ESI+) m/z 552.4 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. filtrationfiltered
  3. custombefore being purified via HPLC (RP C18, 15-85% CH3CN in H2O with 0.1% NH4OH

Sources & evidence

ORD record
ord-bc1fb88e374c46dab79b935c6a6dad07
Source dataset
uspto-grants-2014_09
Patent number
US08846656B2

Reaction notes

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