Acetyl chloride → HCID 57528914, compound

HRID 1454041Notes

Reaction equation

HRID 1454041 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]([C:12]2[O:13][C:14]([CH3:35])=[C:15]([CH2:17][CH2:18][O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[C@H:25]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:24][CH2:23]4)[N:16]=2)[CH:9]=[CH:10][CH:11]=1.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.ClCCl>[C:1]([NH:5][C:6]1[CH:7]=[C:8]([C:12]2[O:13][C:14]([CH3:35])=[C:15]([CH2:17][CH2:18][O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[C@H:25]([CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:24][CH2:23]4)[N:16]=2)[CH:9]=[CH:10][CH:11]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86598050HCID 86598050, compound

Product 1

HCID 57528914HCID 57528914, compoundYield 55.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of DMAP (1.0 mg) and acetyl chloride (9.3 mg, 0.12 mmol) in 1 mL dichloromethane was added a solution of ethyl ((1S)-5-{2-[2-(3-aminophenyl)-5-methyl-1,3-oxazol-4-yl]ethoxy}-2,3-dihydro-1H-inden-1-yl)acetate (25 mg, 0.06 mmol) in dichloromethane (1 mL). Then, triethylamine (0.5 mL) was added and the reaction mixture was stirred for 16 h. The reaction mixture was concentrated under reduced pressure and redissolved in acetonitrile/methanol. The solution was filtered through a C8-Silica plug before preparative HPLC purification using 10 to 80% acetonitrile in water gradient to afford 15.3 mg (55.6%) of the desired product. 1H NMR (300 MHz/CDCl3) δ 7.97 (s, 1H), 7.70 (d, 2H), 7.49 (s, 1H), 7.37 (t, 1H), 7.03 (d, 1H), 6.76 (s, 1H), 6.69 (d, 1H), 4.11-4.22 (m, 4H), 3.48 (qr, 1H), 2.92 (t, 2H), 2.72-2.88 (m, 2H), 2.68 (dd, 1H), 2.27-2.40 (m, 5H), 2.16 (s, 3H), 1.64-1.76 (m, 1H), 1.24 (t, 3H). EI-LCMS(rel abundance), m/z 463.4 (MH+, 100%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionredissolved in acetonitrile/methanol
  3. filtrationThe solution was filtered through a C8-Silica plug before preparative HPLC purification

Sources & evidence

ORD record
ord-0fbd0b520b45485d849ee40a3ff8b148
Source dataset
uspto-grants-2009_01
Patent number
US07476742B2

Reaction notes

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