Pyridine → HCID 178421986, compound

HRID 2053021Notes

Reaction equation

HRID 2053021 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]([CH3:25])[N:8]([C@@H:26]3[CH2:29][C@H:28]([CH2:30]O)[CH2:27]3)[C:4]=2[N:5]=[CH:6][N:7]=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[N:43]1[CH:48]=[CH:47][CH:46]=CC=1>>[N:43]1([CH2:30][C@@H:28]2[CH2:29][C@H:26]([N:8]3[C:4]4[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=4[C:10]([C:11]4[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][C:19]5[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=5)[CH:12]=4)=[C:9]3[CH3:25])[CH2:27]2)[CH2:46][CH2:47][CH2:48]1

Participants

4

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 178421991HCID 178421991, compound

Product 1

HCID 178421986HCID 178421986, compound

Procedure

The title compound is prepared in analogy to Example 116 starting from 0.35 g (0.84 mmol) cis-{3-[4-amino-5-(3-benzyloxy-phenyl)-6-methyl-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutyl}-methanol and 0.328 g (1.69 mmol) p-toluenesulfonyl chloride in 3.5 ml dry pyridine, followed by 0.442 ml (6.33 mmol) trimethylenimine (Fluka, Buchs, Switzerland). Analytical HPLC: tR=9.22 min (Grad 1); ES-MS: m/eo=454.3; NMR (DMSO-d6): 8.08/s (1H), 7.25-7.5/several m's (6H), 7.02/“d” (1H); 6.93/s (1H); 6.89/“d” (1H); 5.4-6.0/b (NH2); 5.13/s (2H); 4.76/m (1H); 3.11/“t” (4H); 2.75-2.90/m (2H); 2.54/d (2H); 2.35-2.45/m (2H); 2.22/s (3H); 2.03/m (1H); 1.9-2.0/m (2H).

Sources & evidence

ORD record
ord-913605b0c742400a9ac78aaae51ec3e4
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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