Acetyl chloride → HCID 9923710, compound

HRID 1835179Notes

Reaction equation

HRID 1835179 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[N:5]1[CH:10]=[CH:9][N:8]=[C:7]2[NH:11][C:12]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:23][CH2:24][CH2:25][NH2:26])[CH:15]=3)=[CH:13][C:6]=12.C(N(CC)CC)C>ClCCl>[N:5]1[CH:10]=[CH:9][N:8]=[C:7]2[NH:11][C:12]([C:14]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]([CH2:23][CH2:24][CH2:25][NH:26][C:1](=[O:3])[CH3:2])[CH:15]=3)=[CH:13][C:6]=12

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 9922078HCID 9922078, compound

Product 1

HCID 9923710HCID 9923710, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (31 μl) was added dropwise to a solution of 3-[3-(5H-pyrrolo[2,3-b]pyrazin-6-yl)-indol-1-yl]-propylamine [100 mg, Example 3(a)] and triethylamine (52.2 μl) and dichloromethane (20 mL) at ambient temperature under a nitrogen atmosphere. After stirring for 24 hours at ambient temperature the reaction mixture was evaporated. The residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (9:1, v/v) to give the title compound (82 mg) as a yellow solid, m.p. 260° C. MS: 334 (MH+).

Workup

  1. customwas evaporated
  2. additionThe residue was subjected to flash chromatography on silica eluting with a mixture of dichloromethane and methanol (9:1

Sources & evidence

ORD record
ord-0373f2f1d78243bc8f5e9c8a37a310a6
Source dataset
uspto-grants-2004_08
Patent number
US06770643B2

Reaction notes

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