HCID 178507513, compound → HCID 178517979, compound

HRID 46141Notes

Reaction equation

HRID 46141 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9](=O)[CH2:10][CH:11]1[S:15][C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:13][C:12]1=[O:23]>CC(O)=O>[NH:16]([C:14]1[S:15][CH:11]([CH2:10][C:9]2[NH:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[N:1]=2)[C:12](=[O:23])[N:13]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

3

Reactant 1

HCID 178507513HCID 178507513, compound

Product 1

HCID 178517979HCID 178517979, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

N-(2-Aminophenyl)-2-(2-anilino-4-oxo-4,5-dihydro-1,3-thiazol-5-yl)acetamide (40.8 mg, 1 eq) was taken up in HOAc (2 mL), transferred to a micro-tube and run at 100° C. for 600 s. The reaction mixture was evaporated to give 42 mg, as a crude brown oil. Purified by HP-LCMS, to the pooled fractions was added NaOH (1M) to pH=14, the MeCN was evaporated and the aqueous layer extracted with DCM/H2O (9:1), dried and evaporated to give the title compound as an off-white powder: HPLC 99%, RT=2.02 min (System A, 10-97% MeCN over 3 min), 99%, RT=0.96 min (System B, 2-95% MeCN over 2 min); 1H NMR (400 MHz, METHANOL-D4) δ ppm 3.23 (m, 1 H), 3.80 (m, 1 H), 4.70 (m, 1 H), 7.02 (m, 1 H), 7.17 (m, 3 H), 7.32 (m, 2 H), 7.50 (m, 2 H), 7.62 (m, 1 H); MS [M+H]+ m/z=323.

Workup

  1. customtransferred to a micro-tube
  2. customThe reaction mixture was evaporated
  3. customto give 42 mg
  4. customPurified by HP-LCMS, to the pooled fractions
  5. additionwas added NaOH (1M) to pH=14
  6. customthe MeCN was evaporated
  7. extractionthe aqueous layer extracted with DCM/H2O (9:1)
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-50bf9376824d4955a42452298bb66b67
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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