4-Chlorobutyryl chloride → HCID 69047340, compound

HRID 1259282Notes

Reaction equation

HRID 1259282 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][C:6]1[C:15]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=2[C:9](=[O:16])[NH:8][N:7]=1.[Cl:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25]>ClCCl>[Cl:20][CH2:21][CH2:22][CH2:23][C:24]([NH:1][C:2]1[CH:19]=[CH:18][CH:17]=[C:4]([CH2:5][C:6]2[C:15]3[CH2:14][CH2:13][CH2:12][CH2:11][C:10]=3[C:9](=[O:16])[NH:8][N:7]=2)[CH:3]=1)=[O:25]

Participants

4

Reactant 2

HCID 783704-Chlorobutyryl chlorideHCID 597557554-(3-Aminobenzyl)-5,6,7,8-tetrahydrophthalazin-1(2h)-one

Product 1

HCID 69047340HCID 69047340, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of EXAMPLE 89 (150 mg, 0.59 mmol) and 4-chlorobutanoyl chloride (83 mg, 0.59 mmol) in dichloromethane (5 mL) was stirred at room temperature for 16 hours, and was concentrated. The residue was partitioned between ethyl acetate and brine. The organic phase was washed with brine, and concentrated to provide the title compound. MS (DCI/NH3) m/z 360 (M+H)+; 1H NMR (400 MHz, CD3OD): δ 1.66-1.73 (m, 4H), 2.07-2.15 (m, 2H), 2.40-2.46 (m, 2H), 2.48-2.51 (m, 2H), 2.50-2.56 (m, 2H), 3.63 (t, J=6.44 Hz, 2H), 3.96 (s, 2H), 6.93 (d, J=7.67 Hz, 1H), 7.21-7.26 (m, 1H), 7.36 (s, 1H), 7.38-7.46 (m, 1H).

Workup

  1. concentrationwas concentrated
  2. customThe residue was partitioned between ethyl acetate and brine
  3. washThe organic phase was washed with brine
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7070f7b8e48442d392314a63c3b09c6d
Source dataset
uspto-grants-2013_06
Patent number
US08466150B2

Reaction notes

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