Ammonium Chloride → HCID 10429705, compound

HRID 1178709Notes

Reaction equation

HRID 1178709 reaction equation
C[Al](C)C.[Cl-].[NH4+:6].C[O:8][C:9]([C:11]1[C:12]([S:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][CH:26]=2)=[N:13][S:14][C:15]=1[NH:16][C:17]1[N:22]=[CH:21][CH:20]=[CH:19][N:18]=1)=O>>[Cl:31][C:28]1[CH:29]=[CH:30][C:25]([CH2:24][S:23][C:12]2[C:11]([C:9]([NH2:6])=[O:8])=[C:15]([NH:16][C:17]3[N:22]=[CH:21][CH:20]=[CH:19][N:18]=3)[S:14][N:13]=2)=[CH:26][CH:27]=1

Participants

4

Reactant 3

HCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 69515353HCID 69515353, compound

Product 1

HCID 10429705HCID 10429705, compoundYield 17%

Conditions

Temperature
80 °C

Procedure

Trimethyl aluminum (2M/toluene, 2.55 mL, 5.1 mmol) is added to a dry flask containing ammonium chloride (272.3 mg, 5.1 mmol). The solution is then allowed to stir for 30 min and is added to a dry flask containing compound 21 (100 mg, 0.26 mmol). The reaction is then heated to 80° C. for 4 hours and then cooled to room temperature. The reaction is then carefully quenched with 1 N HCl and extracted with EtOAc (×3). The combined organics are dried over sodium sulfate, filtered and concentrated in vacuo. Column chromatography (20%→50% EtOAc/methylene chloride) provides 3-(4-Chloro-benzylsulfanyl)-5-(pyrimidin-2-ylamino)-isothiazole-4-carboxylic acid amide (16.2 mg, 17%) in addition to the starting material 21 (36.6 mg). 1H NMR (d6 DMSO): δ 11.61 (1H, br. s), 8.73 (2H, d, J=5.0 Hz), 7.43 (2H, d, J=8.4 Hz), 7.34 (2H, d, J=8.4 Hz), 7.15 (1H, dd, J=5.0, 5.0 Hz), 4.46 (2H, s). LRMS (M+): 378.1, (M−): 376.0.

Workup

  1. additionis added to a dry flask
  2. temperaturecooled to room temperature
  3. customThe reaction is then carefully quenched with 1 N HCl
  4. extractionextracted with EtOAc (×3)
  5. dry with materialThe combined organics are dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d31ec06b16f948999629e63229afbc26
Source dataset
uspto-grants-2007_10
Patent number
US07276602B2

Reaction notes

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