Chloroacetyl chloride → HCID 68199703, compound

HRID 1184420Notes

Reaction equation

HRID 1184420 reaction equation
[NH2:1][C@@H:2]1[CH2:7][CH2:6][C@@H:5]([C:8]([NH:10][CH:11]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:9])[C@H:4]([C:26]2[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=2)[CH2:3]1.[Cl:33][CH2:34][C:35](Cl)=[O:36].CCN(C(C)C)C(C)C>CC#N>[F:25][C:22]1[CH:23]=[CH:24][C:19]([CH:11]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[NH:10][C:8]([C@@H:5]2[CH2:6][CH2:7][C@@H:2]([NH:1][C:35](=[O:36])[CH2:34][Cl:33])[CH2:3][C@H:4]2[C:26]2[CH:31]=[CH:30][C:29]([Br:32])=[CH:28][CH:27]=2)=[O:9])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chloride2×HCID 81531Diisopropylethylamine2×HCID 68199701HCID 68199701, compound

Product 1

HCID 68199703HCID 68199703, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To the product from Example 54 (120 mg, 0.24 mmol) in MeCN (4 mL) was added chloroacetyl chloride (24 mg, 0.3 mmol). The reaction was aged for 90 min at rt and DIEA (45 μL, 0.24 mmol) was added. After 15 min, another portion of chloroacetyl chloride (12 mg, 0.15 mmol) was added, along with DIEA (45 μL, 0.24 mmol). The reaction was concentrated, diluted with CHCl3 and washed with Na2CO3/brine 1:1. The organic layer was dried (Na2SO4), filtered and concentrated to afford the title compound. HPLC/MS: 575.1/577.0 (M+1); Rt=3.36 min.

Workup

  1. waitAfter 15 min
  2. concentrationThe reaction was concentrated
  3. additiondiluted with CHCl3
  4. washwashed with Na2CO3/brine 1:1
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-54480562ed614060be4d4f4f4687b4f6
Source dataset
uspto-grants-2014_03
Patent number
US08669252B2

Reaction notes

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