4-Toluenesulfonyl chloride → HCID 178421989, compound

HRID 2053022Notes

Reaction equation

HRID 2053022 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.[OH:43][CH:44]1[CH2:49][CH2:48][NH:47][CH2:46][CH2:45]1>N1C=CC=CC=1>[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:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)[CH:12]=3)=[C:9]([CH3:25])[N:8]([C@@H:26]3[CH2:29][C@H:28]([CH2:30][N:47]4[CH2:48][CH2:49][CH:44]([OH:43])[CH2:45][CH2:46]4)[CH2:27]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 79341Piperidin-4-olHCID 178421991HCID 178421991, compound

Product 1

HCID 178421989HCID 178421989, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

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 0.87 g (8.44 mmol) 4-hydroxypiperidine (Fluka, Buchs, Switzerland). Analytical HPLC: tR=8.76 min (Grad 1); ES-MS: m/eo=498.2; NMR (DMSO-d6; not all signals reported): 8.07/s (1H), 7.25-7.5/several m's (6H), 7.01/“d” (1H); 6.94/s (1H); 6.89/“d” (1H); 5.13/s (2H); 4.76/m (1H); 4.51/d (OH); 2.22/s (3H).

Sources & evidence

ORD record
ord-e1789883b69549418b82ec652bbe282d
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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