Acetyl chloride → HCID 90031014, compound

HRID 531554Notes

Reaction equation

HRID 531554 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]5)=[CH:23][CH:22]=4)[CH:19]=3)[N:14]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:35])=[O:34])[CH:13]=2)[C:8]([CH3:43])=[N:7]1.C(N(CC)CC)C.[C:54](Cl)(=[O:56])[CH3:55]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:44]=[CH:45][CH:46]=1)[CH2:5][N:6]1[C:10]([CH3:11])=[C:9]([C:12]2[C:20]3[C:15](=[N:16][CH:17]=[C:18]([C:21]4[CH:26]=[CH:25][C:24]([N:27]5[CH2:28][CH2:29][N:30]([C:54](=[O:56])[CH3:55])[CH2:31][CH2:32]5)=[CH:23][CH:22]=4)[CH:19]=3)[N:14]([S:33]([C:36]3[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=3)(=[O:34])=[O:35])[CH:13]=2)[C:8]([CH3:43])=[N:7]1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 90031300HCID 90031300, compound

Product 1

HCID 90031014HCID 90031014, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A stirred solution of 3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-5-(4-(piperazin-1-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.157 mmol), triethylamine (47.8 mg, 0.473 mmol), DCM (3 ml) was added acetyl chloride (18.5 mg, 0.236 mmol) drop wise at 0° C. Reaction mass was gradually warmed to room temperature, reaction completed in an hour. Reaction mass was diluted with DCM and washed with water, dried over sodium sulfate and concentrated to give 98 mg (92.4% yield) of the titled compound. MS: m/z=677.2 (M+1).

Workup

  1. customReaction mass
  2. customreaction
  3. waitcompleted in an hour
  4. customReaction mass
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-d000ffd7c1a64351a8e918e1f4d57fc7
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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