Acetyl chloride → HCID 11153617, compound

HRID 2223401Notes

Reaction equation

HRID 2223401 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:11]=1[O:12][CH3:13])[CH:8]([NH:14][C:15]([NH:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]3[C:19]=1[CH:20]=[N:21][NH:22]3)=[O:16])[CH2:7][CH2:6]2.[C:27](Cl)(=[O:29])[CH3:28].C(OCC)(=O)C>N1C=CC=CC=1>[C:27]([N:22]1[C:23]2[C:19](=[C:18]([NH:17][C:15]([NH:14][CH:8]3[C:9]4[C:5](=[CH:4][C:3]([O:2][CH3:1])=[C:11]([O:12][CH3:13])[CH:10]=4)[CH2:6][CH2:7]3)=[O:16])[CH:26]=[CH:25][CH:24]=2)[CH:20]=[N:21]1)(=[O:29])[CH3:28]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8857Ethyl AcetateHCID 11337110HCID 11337110, compound

Product 1

HCID 11153617HCID 11153617, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To the solution of 1-(5,6-dimethoxy-indan-1-yl)-3-(1H-indazol-4-yl)-urea (0.1 g, 0.28 mmol) in pyridine (2 mL) was added acetyl chloride (0.5 mL) and mixture stirred for 15 hours at ambient temperature. The mixture was suspended with ethyl acetate and filtered. The precipitate was triturated with ether twice and dried to obtain 42 mg (38%) of desired product as a yellow solid. NMR (DMSO-d6): 8.98 (s, 1H), 8.72 (s, 1H), 7.60 (d, J 7.5 Hz, 1H), 7.32-7.18 (m, 2H), 6.90 (d, J 8Hz, 2H), 6.53 (d, J 8 Hz, 1H), 5.16 (m, 1H), 3.76 (s, 3H), 3.72 (s, 3H), 3.00-2.70 (m, 5H), 2.43 (m, 1H), 1.82 (m, 1H). MS (DCI): 395 (M+1). Elemental: Calculated for C18H18N4O2.0.2 H2O: C 63.37, H 5.67, N 14.08; Found: C 63.07, H 5.49, N 13.94.

Workup

  1. filtrationfiltered
  2. customThe precipitate was triturated with ether twice
  3. customdried

Sources & evidence

ORD record
ord-542a97cadd3c4621bfb9c0fac5c38da9
Source dataset
uspto-grants-2008_05
Patent number
US07375126B2

Reaction notes

Loading…