Acetyl chloride → HCID 86727563, compound

HRID 519163Notes

Reaction equation

HRID 519163 reaction equation
Cl.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:22]=[C:21]2[C:12]([N:13]3[C:18]([CH2:19][O:20]2)=[N:17][NH:16][C:15](=[O:23])[C@H:14]3[CH3:24])=[CH:11][C:10]=1[N:25]([CH3:31])[C:26]1([CH3:30])[CH2:29][NH:28][CH2:27]1.CCN(C(C)C)C(C)C.[C:41](Cl)(=[O:43])[CH3:42]>C(Cl)Cl>[C:41]([N:28]1[CH2:27][C:26]([N:25]([CH3:31])[C:10]2[CH:11]=[C:12]3[C:21](=[CH:22][C:9]=2[C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[F:2])[O:20][CH2:19][C:18]2[N:13]3[C@H:14]([CH3:24])[C:15](=[O:23])[NH:16][N:17]=2)([CH3:30])[CH2:29]1)(=[O:43])[CH3:42]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 86727560HCID 86727560, compound

Product 1

HCID 86727563HCID 86727563, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-7-(2-fluoro-phenyl)-4-methyl-6-[methyl-(3-methyl-azetidin-3-yl)-amino]-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one hydrochloride acid (0.125 g, 0.30 mmol) was dissolved in DCM (1 mL) and DIPEA (98 μl, 0.561 mmol) was added. The reaction mixture was stirred at room temperature for 6 min then acetyl chloride (59.8 μl, 0.841 mmol) was added. The reaction mixture was stirred at rt for 10 min and concentrated in vacuo. The residue was purified by basic prep-HPLC (Table 3, Method 32) to give (R)-6-[(1-acetyl-3-methyl-azetidin-3-yl)-methyl-amino]-7-(2-fluoro-phenyl)-4-methyl-2,10-dihydro-9-oxa-1,2,4a-triaza-phenanthren-3-one (0.024 g, 18%). 1H NMR (CD3OD, 400 MHz) δ 7.36-7.33 (m, 2H), 7.25-7.22 (m, 1H), 7.17-7.14 (m, 1H), 6.95-6.92 (m, 2H), 4.80 (m, 1H), 4.68-4.62 (m, 2H), 4.09-4.05 (m, 1H), 3.85-3.73 (m, 2H), 3.55-3.50 (m, 1H), 2.58 (m, 3H), 1.79 (s, 3H), 1.50 (m, 3H), 1.44 (m, 3H). LC/MS (Table 1, Method 4), Rt=2.300 min., MS m/z: 452 [M+H]+.

Workup

  1. stirringThe reaction mixture was stirred at rt for 10 min
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by basic prep-HPLC (Table 3, Method 32)

Sources & evidence

ORD record
ord-2133fe2d824d4ce485780c4d2d252ee8
Source dataset
uspto-grants-2015_08
Patent number
US09115151B2

Reaction notes

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