Acetic Anhydride → HCID 66619161, compound

HRID 218048Notes

Reaction equation

HRID 218048 reaction equation
[N:1]1[C:9]2[CH2:8][CH2:7][NH:6][CH2:5][C:4]=2[S:3][C:2]=1[C:10]1([C:16]2[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=2)[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1.[CH3:25][C:26](OC(C)=O)=[O:27]>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[C:26]([N:6]1[CH2:7][CH2:8][C:9]2[N:1]=[C:2]([C:10]3([C:16]4[CH:24]=[CH:23][C:19]([C:20]([OH:22])=[O:21])=[CH:18][CH:17]=4)[CH2:11][CH2:12][O:13][CH2:14][CH2:15]3)[S:3][C:4]=2[CH2:5]1)(=[O:27])[CH3:25]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 66619535HCID 66619535, compound

Product 1

HCID 66619161HCID 66619161, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

4-[4-(4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-tetrahydro-pyran-4-yl]-benzoic acid (40 mg, 0.116 mmol) in pyridine, catalytic amount of 4-dimethylaminopyridine (DMAP), and excess Ac2O were mixed together at room temperature. After the reaction was complete, the mixture was evaporated, washed with water, and extracted with EtOAc. The organic phase was dried and evaporated to give 4-[4-(5-acetyl-4,5,6,7-tetrahydro-thiazolo[5,4-c]pyridin-2-yl)-tetrahydro-pyran-4-yl]-benzoic acid. Similar HATU coupling procedure from Example 9 was followed to obtain the title compound. MS found for C26H28N4O3S as (M+H)+477.58. 1H NMR (400 MHz, dmso-d6): δ: 9.53 (s, 1H), 7.89 (d, J=8.4 Hz, 2H), 7.51 (t, J=8.4 Hz, 2H), 7.10 (d, J=7.2 Hz, 1H), 6.92 (t, J=7.6 Hz, 1H), 6.72 (d, J=8.0 Hz, 1H), 6.54 (t, J=7.6 Hz, 1H), 4.84 (s, 2H), 4.61-4.57 (m, 2H), 3.69-3.57 (m, 6H), 2.80-2.29 (m, 6H), 2.05-1.98 (m, 3H).

Workup

  1. customthe mixture was evaporated
  2. washwashed with water
  3. extractionextracted with EtOAc
  4. customThe organic phase was dried
  5. customevaporated

Sources & evidence

ORD record
ord-a8b5a41b78ad4d61873858669e6c301d
Source dataset
uspto-grants-2012_06
Patent number
US08198299B2

Reaction notes

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