Water → HCID 57986905, compound

HRID 2063441Notes

Reaction equation

HRID 2063441 reaction equation
[N:1]1([C:6]2[CH:31]=[CH:30][C:9]([O:10][CH2:11][C:12]3[N:13]=[C:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:23]5[N:28]=[CH:27][C:26]([NH2:29])=[CH:25][N:24]=5)[CH2:19][CH2:18]4)[S:15][CH:16]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1.C(N(CC)CC)C.[C:39](Cl)(=[O:41])[CH3:40].O>C(Cl)Cl>[N:1]1([C:6]2[CH:31]=[CH:30][C:9]([O:10][CH2:11][C:12]3[N:13]=[C:14]([CH:17]4[CH2:18][CH2:19][N:20]([C:23]5[N:28]=[CH:27][C:26]([NH:29][C:39](=[O:41])[CH3:40])=[CH:25][N:24]=5)[CH2:21][CH2:22]4)[S:15][CH:16]=3)=[CH:8][CH:7]=2)[CH:5]=[N:4][N:3]=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 57986823HCID 57986823, compound

Product 1

HCID 57986905HCID 57986905, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2-{4-[4-(4-Tetrazol-1-yl-phenoxymethyl)-thiazol-2-yl]-piperidin-1-yl}-pyrimidin-5-ylamine (Example 107) (0.321 mmol) was dissolved in DCM and triethylamine (2 eq.) was added. The reaction was cooled to 0° C., acetylchloride (1 eq.) was added dropwise and the reaction was stirred at room temperature overnight. Water was added and the mixture was extracted with ethyl acetate, dried over sodium sulfate, filtered and concentrated under reduced pressure. Silica gel chromatography of the resulting oil (DCM/MeOH) provided the expected product. 1H NMR (CDCl3): δ 8.84 (1H, s), 8.36 (2H, s), 7.55 (2H, m), 7.19 (1H, s), 7.11 (2H, m), 6.94 (1H, s), 5.16 (2H, s), 4.77 (2H, m), 3.25 (1H, m), 3.01 (2H, m), 2.16 (2H, m), 2.15 (3H, s), 1.75 (2H, m).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a91d3ccb964346fcb9636fe3232aa33a
Source dataset
uspto-grants-2012_10
Patent number
US08288384B2

Reaction notes

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