Triethylamine → HCID 68195278, compound

HRID 2169547Notes

Reaction equation

HRID 2169547 reaction equation
[Si:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[N:26]=[CH:25][C:24]4[NH:23][CH2:22][CH:21]5[CH2:27][O:28][CH2:29][CH2:30][N:20]5[C:19]=4[N:18]=3)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([CH2:39][C:40](Cl)=[O:41])=[CH:35][CH:34]=1.C(N(CC)CC)C>C(Cl)Cl>[Si:1]([N:8]1[C:16]2[C:11](=[C:12]([C:17]3[N:26]=[CH:25][C:24]4[N:23]([C:40](=[O:41])[CH2:39][C:36]5[CH:37]=[CH:38][C:33]([O:32][CH3:31])=[CH:34][CH:35]=5)[CH2:22][CH:21]5[CH2:27][O:28][CH2:29][CH2:30][N:20]5[C:19]=4[N:18]=3)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27346884-Methoxyphenylacetyl chlorideHCID 68194818HCID 68194818, compound

Product 1

HCID 68195278HCID 68195278, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-(1-(tert-Butyldimethylsilyl)-1H-indol-4-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x12, 42 mg, 0.100 mmol) in CH2Cl2 (1 mL) was cooled to 0° C. 2-(4-Methoxyphenyl)acetyl chloride (0.018 mL, 0.120 mmol) was added, followed by triethylamine (0.028 mL, 0.199 mmol) to give a yellow solution. The reaction mixture was stirred for 2 hours at 0° C. The solvent was subsequently removed in vacuo and the resulting concentrate was loaded onto an ISCO® silica gel cartridge (4 g) and eluted using an ethyl acetatehexane gradient. The product was collected and concentrated in vacuo to afford the title compound as a yellow oil (42 mg, 74%). 1H NMR (400 MHz, DMSO-d6) δ 0.64 (s, 6 H), 0.89 (s, 9 H), 3.02-3.22 (m, 4 H), 3.42-3.61 (m, 2 H), 3.66-3.78 (m, 3 H), 3.87-3.92 (m, 2 H), 3.91-3.98 (m, 1 H), 4.30-4.47 (m, 1 H), 4.64-4.75 (m, 1 H), 6.79-6.93 (m, 2 H), 7.00-7.30 (m, 3 H), 7.42-7.51 (m, 2 H), 7.61-7.68 (m, 1 H), 8.02-8.07 (m, 1 H), 8.32-9.02 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C32H39N5O3Si, 570.28; found 570.6.

Workup

  1. customto give a yellow solution
  2. customThe solvent was subsequently removed in vacuo
  3. concentrationthe resulting concentrate
  4. washeluted
  5. customThe product was collected
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8f5650e430ca45b2ac8080b20c209bc8
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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