4-Toluenesulfonyl chloride → HCID 178435363, compound

HRID 2053028Notes

Reaction equation

HRID 2053028 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[CH:12]=3)=[C:9]([CH2:25][CH3:26])[N:8]([C@@H:27]3[CH2:30][C@H:29]([CH2:31]O)[CH2:28]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[NH:44]1[CH2:48][CH2:47][CH2:46][CH2:45]1>N1C=CC=CC=1>[CH2:18]([O:17][C:13]1[CH:12]=[C:11]([C:10]2[C:3]3[C:2]([NH2:1])=[N:7][CH:6]=[N:5][C:4]=3[N:8]([C@H:27]3[CH2:28][C@@H:29]([CH2:31][N:44]4[CH2:48][CH2:47][CH2:46][CH2:45]4)[CH2:30]3)[C:9]=2[CH2:25][CH3:26])[CH:16]=[CH:15][CH:14]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 31268PyrrolidineHCID 178435367HCID 178435367, compound

Product 1

HCID 178435363HCID 178435363, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound is prepared in a one pot reaction in analogy to Example 116 starting from 0.2 g (0.46 mmol) cis-{3-[4-amino-5-(3-benzyloxy-phenyl)-6-ethyl-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutyl}-methanol of Example 124 and 0.18 g (0.92 mmol) p-toluenesulfonyl chloride in 2 ml dry pyridine followed by 2 ml pyrrolidine. The reaction is controlled by tlc. Analytical HPLC: tR=9.61 min (Grad 1); ES-MS: m/eo=482.0; NMR (DMSO-d6; not all signals reported): 8.12/s (1H); 6.9-7.5/several m's (6H), 7.05/“d” (1H); 6.95/s (1H); 6.92/“d” (1H); 5.4-6.0/b (NH2); 5.15/s (2H); 4.72/m (1H); 2.62/q (2H); 1.06/t (3H).

Sources & evidence

ORD record
ord-3aa1c012dea242359526b879ddc6ae42
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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