1,2-Dichloroethane → HCID 71625350, compound

HRID 1509012Notes

Reaction equation

HRID 1509012 reaction equation
[O:1]=[S:2]1(=[O:29])[C:11]2[C:10]([NH:12][C:13]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]([OH:22])=O)=[CH:15][CH:14]=3)=[N:9][C:8]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:7][C:6]=2[CH2:5][CH2:4][CH2:3]1.C(Cl)CCl.C1C=[CH:36][C:37]2N(O)N=[N:40][C:38]=2C=1.C(N)CC>CN(C=O)C.C(OCC)(=O)C>[O:1]=[S:2]1(=[O:29])[C:11]2[C:10]([NH:12][C:13]3[CH:14]=[CH:15][C:16]([CH2:19][C:20]([NH:40][CH2:38][CH2:37][CH3:36])=[O:22])=[CH:17][CH:18]=3)=[N:9][C:8]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)=[N:7][C:6]=2[CH2:5][CH2:4][CH2:3]1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 7852PropylamineHCID 757711-HydroxybenzotriazoleHCID 71624964HCID 71624964, compound

Product 1

HCID 71625350HCID 71625350, compoundYield 87.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-(4-((5,5-dioxido-2-phenyl-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidin-4-yl)amino)phenyl)acetic acid (0.115 g, 0.28 mmol) in DMF (4 mL) was added EDC (0.107 g, 0.56 mmol), HOBT (0.076 g, 0.56 mmol) and n-propylamine (0.12 mL, 1.4 mmol). The mixture was stirred at rt for 16 h. The mixture was diluted with ethyl acetate and then washed with water. The organic layer were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the desired product (0.110 g, 87%) as a white solid. MW=450.55. 1H NMR (DMSO-d6, 500 MHz) δ 8.74 (s, 1H), 8.29-8.25 (m, 2H), 8.05-7.99 (m, 1H), 7.63-7.49 (m, 5H), 7.33 (d, J=8.5 Hz, 2H), 3.76-3.71 (m, 2H), 3.42 (s, 2H), 3.10-2.99 (m, 4H), 2.42-2.35 (m, 2H), 1.45-1.38 (m, 2H), 0.85 (t, J=7.5 Hz, 3H); APCI MS m/z 451 [M+H]+.

Workup

  1. washwashed with water
  2. dry with materialThe organic layer were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated
  5. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

Sources & evidence

ORD record
ord-39e18ca542b44ff49638234886029f52
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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