Chloroacetyl chloride → HCID 67347355, compound

HRID 1257662Notes

Reaction equation

HRID 1257662 reaction equation
[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH2:33])[C:18]([NH:19][CH:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH2:22][CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[Cl:41][CH2:42][C:43](Cl)=[O:44]>C(Cl)Cl>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH:33][C:43](=[O:44])[CH2:42][Cl:41])[C:18]([NH:19][CH:20]4[CH2:25][CH2:24][N:23]([CH2:26][C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)[CH2:22][CH2:21]4)=[C:13]3[CH:12]=[CH:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 58394937HCID 58394937, compound

Product 1

HCID 67347355HCID 67347355, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To an ice-cold mixture of 1-benzenesulfonyl-N*4*-(1-benzyl-piperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine 1.30 g, 2.80 mmol) and triethylamine (0.59 mL, 4.20 mmol) in DCM (50 mL) was added chloroacetyl chloride (0.25 mL, 3.10 mmol) and the mixture was stirred 2 h. The reaction mixture was diluted with DCM, washed with water, brine, and dried over sodium sulphate. The residue was purified by flash (silica gel. 0-5% MeOH/DCM) to afford N-[1-Benzenesulfonyl-4-(1-benzyl-piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridin-5-yl]-2-chloro-acetamide (1.10 g, 72%): LCMS (method E, ESI): RT=1.2 min; m+1=538.2.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over sodium sulphate
  3. customThe residue was purified by flash (silica gel. 0-5% MeOH/DCM)

Sources & evidence

ORD record
ord-ad5cc5db30f94ff2aedad5a47c036e25
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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