Methoxyacetyl chloride → HCID 57585051, compound

HRID 2077580Notes

Reaction equation

HRID 2077580 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH2:15])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19].[CH3:21][O:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)Cl.N1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]3[N:12]=[C:13]([NH:15][C:24](=[O:25])[CH2:23][O:22][CH3:21])[S:14][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[N:18]([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 96623Methoxyacetyl chloride2×HCID 57584985HCID 57584985, compound

Product 1

HCID 57585051HCID 57585051, compoundYield 82.5%

Reagents, catalysts & solvents 1

HCID 21875418Pyridine methylene chlorideSolvent

Procedure

A mixture of 6-(6-chloro-5-(dimethylamino)pyridin-3-yl)benzo[d]thiazol-2-amine (54 mg, 177 μmol) and 2-methoxyacetyl chloride (25 mg, 230 μmol) in DCM-pyridine (0.5 mL each) was stirred at rt. More 2-methoxyacetyl chloride (25 mg, 230 μmol) was added after overnight, resulting in a solution. The reaction was complete after 1 h. The mixture was concentrated, and diluted with NaHCO3 (saturated, 5 mL). After agitating for 30 min, the mixture was filtered, and washed with H2O (3×3 mL) to give a green solid (55 mg, 82%). LCMS: calc'd for C17H17ClN4O2S:376.0. found: 377.1. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.86 (s, 6H) 3.32 (s, 3H) 4.23 (s, 2H) 7.76-7.88 (m, 3H) 8.36 (s, 1H) 8.43 (s, 1H) 12.39 (s, 1H).

Workup

  1. customresulting in a solution
  2. concentrationThe mixture was concentrated
  3. additiondiluted with NaHCO3 (saturated, 5 mL)
  4. stirringAfter agitating for 30 min
  5. filtrationthe mixture was filtered
  6. washwashed with H2O (3×3 mL)

Sources & evidence

ORD record
ord-099c626c70b64592b21df8fa0673261c
Source dataset
uspto-grants-2011_04
Patent number
US07928140B2

Reaction notes

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