4-Cyanobenzenesulfonyl chloride → HCID 59095495, compound

HRID 251492Notes

Reaction equation

HRID 251492 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[N:10]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[CH:9]=2)=[CH:4][C:3]=1[O:23][CH3:24].[C:25]([C:27]1[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1)#[N:26]>N1C=CC=CC=1>[NH2:17][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:33]([C:30]4[CH:29]=[CH:28][C:27]([C:25]#[N:26])=[CH:32][CH:31]=4)(=[O:35])=[O:34])=[C:3]([O:23][CH3:24])[CH:4]=3)=[CH:9][N:10]([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[C:11]=2[N:12]=[CH:13][N:14]=1

Participants

4

Reactant 2

HCID 394974-Cyanobenzenesulfonyl chlorideHCID 539252325-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 59095495HCID 59095495, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 5-(4-amino-3-methoxyphenyl)-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine (0.026 g, 0.08 mmol), 4-cyanobenzenesulfonyl chloride (0.019 g, 0.10 mmol) and pyridine (0.40 ml) was stirred at room temperature overnight. Most of pyridine was removed under reduced pressure and the residue was purified by preparative RP-HPLC (Rainin C18, 8 μm, 300 A, 25 cm; 25%-100% acetonitrile-0.1M ammonium acetate over 25 min, 21 ml/min) to give N1-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxy-phenyl]-4-cyano-1-benzenesulfonamide as yellow solids (0.018 g, 0.04 mmol): 1H NMR (DMSO-d6, 400 MHz) δ 9.91 (s, 1H), 8.13 (s, 1H), 8.05 (d, 2H), 7.89 (d, 2H), 7.44 (s, 1H), 7.27 (d, 1H), 7.00 (dd, 1H), 6.98 (d, 1H), 6.07 (broad, 2H), 5.07 (m, 1H), 3.49 (s, 3H), 2.11 (m, 2H), 1.88 (m, 4H), 1.69 (m, 2H); MH+489; TLC (ethyl acetate/methanol=9:1) Rf 0.49; RP-HPLC (Hypersil C18, 5 μm, 200 A, 25 cm; 25%-100% acetonitrile-0.1M ammonium acetate over 25 min, 1 ml/min) Rt 14.65 min.

Workup

  1. customMost of pyridine was removed under reduced pressure
  2. customthe residue was purified by preparative RP-HPLC (Rainin C18, 8 μm, 300 A, 25 cm
  3. wait25%-100% acetonitrile-0.1M ammonium acetate over 25 min

Sources & evidence

ORD record
ord-6c77806f656c44a691f446182448b6d0
Source dataset
uspto-grants-2011_01
Patent number
US07863444B2

Reaction notes

Loading…