Water → HCID 50938977, compound

HRID 1971685Notes

Reaction equation

HRID 1971685 reaction equation
[CH:1]([N:4]1[C:32](=[O:33])[C:31]2[N:12]3[CH2:13][CH2:14][C:15]4[CH:16]=[C:17]([O:29][CH3:30])[C:18]([C:21]5[C:22]([CH3:28])=[N:23][N:24]([CH3:27])[C:25]=5[CH3:26])=[CH:19][C:20]=4[C:11]3=[C:10]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)[C:9]=2[CH2:8][NH:7][CH2:6][CH2:5]1)([CH3:3])[CH3:2].[C:39](OC(=O)C)(=[O:41])[CH3:40].O.C(OCC)(=O)C>N1C=CC=CC=1.CN(C1C=CN=CC=1)C>[C:39]([N:7]1[CH2:8][C:9]2[C:10]([C:34]3[S:35][CH:36]=[CH:37][CH:38]=3)=[C:11]3[C:20]4[CH:19]=[C:18]([C:21]5[C:22]([CH3:28])=[N:23][N:24]([CH3:27])[C:25]=5[CH3:26])[C:17]([O:29][CH3:30])=[CH:16][C:15]=4[CH2:14][CH2:13][N:12]3[C:31]=2[C:32](=[O:33])[N:4]([CH:1]([CH3:3])[CH3:2])[CH2:5][CH2:6]1)(=[O:41])[CH3:40]

Participants

7

Reactant 4

HCID 962WaterHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 58124924HCID 58124924, compound

Product 1

HCID 50938977HCID 50938977, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To 32 mg of 10q in 200 μl of pyridine 30 μl of acetic anhydride and 1 mg of DMAP were added. The mixture was stirred for ½ hr, then water and ethyl acetate were added and stirring was continued for ½ hr at RT. The product was extracted into ethyl acetate and washed twice with water, dried, concentrated and the residues were treated with diethyl ether to provide 25 mg of 10r, as white crystalline material. Mp: 178-180° C. Rf 0.15 (heptane/acetone 1/1). NMR (CDCl3) δ 1.33 (bm, 6, N-isoC3H7), 1.90+1.94 (2×s, 6, 2×CH3-pyrrazole), 2.00 (s, 3, N—CH3), 3.70 (s, 3, NCH3), 3.80 (s, 3, OCH3), 4.65 (m, 1, CH isoC3H7), 6.79 and 6.89 (2×s, 2, ArH), 6.93, 7.08 and 7.36 (3×m, 3, thiophene).

Workup

  1. stirringstirring
  2. waitwas continued for ½ hr at RT
  3. extractionThe product was extracted into ethyl acetate
  4. washwashed twice with water
  5. customdried
  6. concentrationconcentrated
  7. additionthe residues were treated with diethyl ether

Sources & evidence

ORD record
ord-b8726567622146e79992763371295df9
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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