Acetic Anhydride → HCID 58691396, compound

HRID 1594473Notes

Reaction equation

HRID 1594473 reaction equation
[CH2:1]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[CH2:11][N:12]([CH3:40])[C:13]1[C:18]([C:19]2[N:24]=[CH:23][N:22]=[C:21]([O:25][C:26]3[C:31]4[N:32]=[C:33]([NH2:35])[S:34][C:30]=4[CH:29]=[CH:28][CH:27]=3)[CH:20]=2)=[CH:17][CH:16]=[C:15]([C:36]([F:39])([F:38])[F:37])[N:14]=1)[CH:2]([CH3:4])[CH3:3].[C:41](OC(=O)C)(=[O:43])[CH3:42]>N1C=CC=CC=1>[CH2:1]([N:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[CH2:11][N:12]([CH3:40])[C:13]1[C:18]([C:19]2[N:24]=[CH:23][N:22]=[C:21]([O:25][C:26]3[C:31]4[N:32]=[C:33]([NH:35][C:41](=[O:43])[CH3:42])[S:34][C:30]=4[CH:29]=[CH:28][CH:27]=3)[CH:20]=2)=[CH:17][CH:16]=[C:15]([C:36]([F:38])([F:37])[F:39])[N:14]=1)[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 58691408HCID 58691408, compound

Product 1

HCID 58691396HCID 58691396, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 4-(6-(2-(((1-isobutylpiperidin-2-yl)methyl)(methyl)amino)-6-(trifluoromethyl)pyridin-3-yl)pyrimidin-4-yloxy)benzo[d]thiazol-2-amine, Example 24(d), (0.14 g, 0.24 mmol) and acetic anhydride (5 mL, Aldrich) in pyridine (20 mL) was stirred at 25° C. for 24 h. The reaction mixture was partitioned between aqueous solution of NaHCO3 and EtOAc. The organic phase was separated, washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. Purification of the residue by silica gel column chromotography (gradient: 50-100% EtOAc/hexane) afforded the title compound as a yellow solid. MS (ESI, pos. ion.) m/z: 614 (M+1). Mp: 123.2-125.4° C.

Workup

  1. customThe reaction mixture was partitioned between aqueous solution of NaHCO3 and EtOAc
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customPurification of the residue by silica gel column chromotography (gradient: 50-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-37aeb8879fcc4a87a043d22bfb04fb6f
Source dataset
uspto-grants-2007_11
Patent number
US07301022B2

Reaction notes

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