Trifluoroacetic acid → HCID 87364290, compound

HRID 1257648Notes

Reaction equation

HRID 1257648 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:34](O)([C:36]([F:39])([F:38])[F:37])=[O:35]>>[C:1]1([S:7]([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([NH:33][C:34](=[O:35])[C:36]([F:39])([F:38])[F:37])[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

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58394937HCID 58394937, compound

Product 1

HCID 87364290HCID 87364290, compound

Procedure

1-Benzenesulfonyl-N*4*-(1-benzyl-piperidin-4-yl)-1H-pyrrolo[2,3-b]pyridine-4,5-diamine (500 mg, 1.08 mmol) in TFA (5 mL) was heated to reflux for 5 hours. After cooling the mixture was concentrated under vacuum affording N-[1-benzenesulfonyl-4-(1-benzyl-piperidin-4-ylamino)-1H-pyrrolo[2,3-b]pyridine-5-yl]-2,2,2-trifluoro-acetamide as an orange residue which was used for the next step without further purification. LCMS (Method B, ESI): RT=2.68 min, m+H=558.35.

Workup

  1. temperatureto reflux for 5 hours
  2. temperatureAfter cooling the mixture
  3. concentrationwas concentrated under vacuum

Sources & evidence

ORD record
ord-7bbb301063e8445286a1d1a58d265702
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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