Acetic Acid → HCID 178477985, compound

HRID 1926632Notes

Reaction equation

HRID 1926632 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[S:12][C:13]=1[C:14]([NH2:16])=O.COC(OC)[N:26]([CH3:28])C.C(O)(=O)C.O.[NH2:36]N>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[N:10]=[C:11]([N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[S:12][C:13]=1[C:14]1[NH:26][CH:28]=[N:36][N:16]=1

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 592500274-(2,4-Dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carboxamide

Product 1

HCID 178477985HCID 178477985, compoundYield 43.6%

Procedure

A mixture of 4-(2,4-dichlorophenyl)-2-morpholin-4-yl-1,3-thiazole-5-carboxamide (23 mg, 0.06 mmol) and 1,1-dimethoxy-N,N-dimethylmethanamine (0.8 mL, 6 mol) was irradiated in the microwave at 160° C. (300 watts) for 30 minutes. The reaction was concentrated in vacuo. The residue dissolved in acetic acid (1.0 mL, 0.18 mol) and hydrazine hydrate (30 mg, 0.7 mmol) and subjected to microwave irradiation at 120° C. (300 watts) for 15 minutes. The solvent was removed in vacuo, the residue was diluted with water (1 mL), the precipitate was collected, washed with water (1 mL) and dried to afford the title compound (10 mg, 40%). LCMS: (FA) ES+, 382. 1H NMR (400 MHz, d6-DMSO) δ: 13.9 (s, 1H), 8.42 (s, 1H), 7.63 (d, 1H), 7.44-7.42 (m, 2H), 3.73-3.70 (m, 4H), 3.44-3.42 (m, 4H).

Workup

  1. customwas irradiated in the microwave at 160° C. (300 watts) for 30 minutes
  2. concentrationThe reaction was concentrated in vacuo
  3. customirradiation at 120° C. (300 watts) for 15 minutes
  4. customThe solvent was removed in vacuo
  5. additionthe residue was diluted with water (1 mL)
  6. customthe precipitate was collected
  7. washwashed with water (1 mL)
  8. customdried

Sources & evidence

ORD record
ord-9acafeda806e4e2d94b4087662d2f853
Source dataset
uspto-grants-2012_05
Patent number
US08183240B2

Reaction notes

Loading…