Ammonia → N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzenesulphonamide

HRID 611547Notes

Reaction equation

HRID 611547 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15](Cl)=[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]1([S:31](Cl)(=[O:33])=[O:32])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[NH3:35]>N1C=CC=CC=1.ClCCl>[NH2:35][C:15]1[C:16]2[C:8]([C:5]3[CH:6]=[CH:7][C:2]([NH:1][S:31]([C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)(=[O:33])=[O:32])=[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

6

Reactant 3

HCID 222AmmoniaHCID 7369Benzenesulfonyl chlorideHCID 541919345-(4-Amino-3-methoxyphenyl)-4-chloro-7-cyclopentylpyrrolo[2,3-d]pyrimidine

Product 1

HCID 9956039N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzenesulphonamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

5-(4-Amino-3-methoxyphenyl)-4-chloro-7-cyclopentylpyrrolo[2,3-d]pyrimidine (0.50 g, prepared in a similar manner to Example 32) was reacted with benzenesulphonyl chloride (0.31 g) in pyridine (5 ml) and dichloromethane (1 ml) at 0° C. and the product obtained after work-up was reacted with ammonia in a similar manner to Example 32 to give N-[4-(4-amino-7-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methoxyphenyl]benzenesulphonamide, m.p. 113-115° C. The structure was confirmed by 1H nmr and mass spectra.

Workup

  1. customthe product obtained after work-up

Sources & evidence

ORD record
ord-341f07793d3f480084859d0d03107fff
Source dataset
uspto-grants-1999_12
Patent number
US06001839

Reaction notes

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