2,2-Dimethoxypropane → HCID 11420805, compound

HRID 2054416Notes

Reaction equation

HRID 2054416 reaction equation
[NH2:1][C:2]1([C:30]([NH2:32])=[O:31])[CH2:5][N:4]([C:6]2[N:11]3[N:12]=[C:13]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=4[Cl:28])[C:14]([C:15]4[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=4)=[C:10]3[N:9]=[C:8]([CH3:29])[N:7]=2)[CH2:3]1.CO[C:35](OC)([CH3:37])[CH3:36]>C1(C)C=CC=CC=1.C(O)(=O)C>[Cl:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:13]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]([Cl:21])=[CH:19][CH:20]=2)=[C:10]2[N:9]=[C:8]([CH3:29])[N:7]=[C:6]([N:4]3[CH2:3][C:2]4([C:30](=[O:31])[NH:32][C:35]([CH3:37])([CH3:36])[NH:1]4)[CH2:5]3)[N:11]2[N:12]=1

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 11190558HCID 11190558, compound

Product 1

HCID 11420805HCID 11420805, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 1140TolueneSolvent

Procedure

To a mixture of 3-amino-1-[7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-azetidine-3-carboxylic acid amide (3A-6; 27 mg, 0.057 mmol) and 2,2-dimethoxypropane (0.75 ml, 6.1 mmol) in toluene (1.3 ml) was added acetic acid (5 drops). After stirring at reflux for 18 hours, the reaction was cooled and extracted from saturated aqueous NaHCO3 with ethyl acetate. The combined extracts were dried (MgSO4), concentrated, in vacuo, and then purified on a Biotage™ Flash 12S column using 0-5% methanol in methylene chloride as eluant to afford after drying, in vacuo, 4A-1 (16 mg, 55%) as an off-white solid: +ESI MS (M+1) 508.1; 1H NMR (400 MHz, DMSO-d6) δ 8.60 (s, 1H), 7.56-7.42 (m, 4H), 7.34-7.30 (m, 4H), 4.92 (d, J=10.4 Hz, 1H), 4.73 (d, J=10.4 Hz, 1H), 4.43 (d, J=10.4 Hz, 1H), 4.19 (d, J=10.4 Hz, 1H), 2.40 (s, 3H), 1.23 (s, 3H), 1.20 (s, 3H).

Workup

  1. temperatureat reflux for 18 hours
  2. temperaturethe reaction was cooled
  3. extractionextracted from saturated aqueous NaHCO3 with ethyl acetate
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated, in vacuo
  6. custompurified on a Biotage™ Flash 12S column
  7. customto afford
  8. customafter drying, in vacuo, 4A-1 (16 mg, 55%) as an off-white solid

Sources & evidence

ORD record
ord-597a21ef1cf540c4bf2c11613e2d6d66
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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