Benzenesulfonamide, 3-amino- → 4-(3-Sulfamoyl-phenylamino)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide

HRID 1391485Notes

Reaction equation

HRID 1391485 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([N:20]3[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]3)[CH:11]=2)=[CH:4][C:3]=1[NH:27][C:28]([N:30]1[C:34]2[N:35]=[CH:36][N:37]=[C:38](Cl)[C:33]=2[CH:32]=[CH:31]1)=[O:29].[NH2:40][C:41]1[CH:42]=[C:43]([S:47]([NH2:50])(=[O:49])=[O:48])[CH:44]=[CH:45][CH:46]=1>C(O)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:26])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([N:20]3[CH:24]=[C:23]([CH3:25])[N:22]=[CH:21]3)[CH:11]=2)=[CH:4][C:3]=1[NH:27][C:28]([N:30]1[C:34]2[N:35]=[CH:36][N:37]=[C:38]([NH:40][C:41]3[CH:46]=[CH:45][CH:44]=[C:43]([S:47](=[O:49])(=[O:48])[NH2:50])[CH:42]=3)[C:33]=2[CH:32]=[CH:31]1)=[O:29]

Participants

4

Reactant 2

HCID 7377Benzenesulfonamide, 3-amino-HCID 596739784-Chloro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide

Product 1

HCID 117872954-(3-Sulfamoyl-phenylamino)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amideYield 57%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

4-Chloro-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide, (50 mg, 0.09 mmol), prepared as in reference 3, in glacial acetic acid (2 mL) is mixed with 3-aminobenzenesulfonamide (31 mg, 0.18 mmol) and shaken at 80° C. for 24 hours. The resulting mixture is directly purified by preparative HPLC-MS to give 4-(3-sulfamoyl-phenylamino)-pyrrolo[2,3-d]pyrimidine-7-carboxylic acid {2-methyl-5-[3-(4-methyl-imidazol-1-yl)-5-trifluoromethyl-benzoylamino]-phenyl}-amide (35.3 mg, yield 57%); 1H NMR (400 MHz, DMSO-d6) δ 11.51 (s, 1H), 10.64 (s, 1H), 10.10 (s, 1H), 9.58 (s, 1H), 8.60 (s, 1H), 8.58 (s, 1H), 8.51 (s, 1H), 8.50 (s, 1H), 8.29 (s, 1H), 8.17 (d, J=8.1 Hz, 1H), 8.14 (s, 1H), 7.87 (d, J=3.9 Hz, 1H), 7.59 (d, J=1.8 Hz, 1H), 7.57 (d, J=7.6 Hz, 1H), 7.53 (d, 5.9 Hz, 1H), 7.37 (s, 2H), 7.30 (d, J=8.5 Hz, 1H), 7.11 (d, J=3.9 Hz, 1H), 2.44 (s, 3H), 2.33 (s, 3H); ESIMS m/z 690.1 (M++1).

Workup

  1. customThe resulting mixture is directly purified by preparative HPLC-MS

Sources & evidence

ORD record
ord-851679509ccb49b1a24377040d0456df
Source dataset
uspto-grants-2008_03
Patent number
US07338957B2

Reaction notes

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