Methanol → HCID 86244451, compound

HRID 252739Notes

Reaction equation

HRID 252739 reaction equation
FC(F)(F)C(O)=O.[Cl:8][C:9]1[N:14]=[N:13][C:12]([C:15]2[S:19][C:18]([NH:20][C:21](=[O:23])[CH3:22])=[N:17][C:16]=2[CH3:24])=[CH:11][C:10]=1[NH:25]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>ClCCl>[NH2:25][C:10]1[CH:11]=[C:12]([C:15]2[S:19][C:18]([NH:20][C:21](=[O:23])[CH3:22])=[N:17][C:16]=2[CH3:24])[N:13]=[N:14][C:9]=1[Cl:8]

Participants

5

Reactant 3

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 86620416HCID 86620416, compound

Product 1

HCID 86244451HCID 86244451, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoroacetic acid (1.5 mL) was added to a stirred mixture of N-[5-(6-chloro-5-tritylaminopyridazin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide (300 mg), methanol (0.5 mL) and dichloromethane (4 mL) that had been cooled to 0° C. The resultant mixture was heated to 55° C. for 5 hours. The mixture was evaporated and the residue was basified to pH8 by the addition of a saturated aqueous sodium bicarbonate solution. The resultant solid was isolated and washed with diethyl ether. The solid was dissolved in dichloromethane and a 7M methanolic ammonia solution was added. The mixture was evaporated to give N-[5-(5-amino-6-chloropyridazin-3-yl)-4-methyl-1,3-thiazol-2-yl]acetamide as a solid; Mass Spectrum: M+H+ 282.

Workup

  1. customThe mixture was evaporated
  2. additionthe residue was basified to pH8 by the addition of a saturated aqueous sodium bicarbonate solution
  3. customThe resultant solid was isolated
  4. washwashed with diethyl ether
  5. dissolutionThe solid was dissolved in dichloromethane
  6. additiona 7M methanolic ammonia solution was added
  7. customThe mixture was evaporated

Sources & evidence

ORD record
ord-b6bac9a015de4fb2ac6d5054d9adb6a9
Source dataset
uspto-grants-2011_01
Patent number
US07868188B2

Reaction notes

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