4-Toluenesulfonyl chloride → HCID 178435364, compound

HRID 2053031Notes

Reaction equation

HRID 2053031 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[CH2:50][CH2:49][CH2:48][C@@H:45]1[CH2:46][OH:47]>>[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]([CH2:25][CH3:26])[N:8]([C@@H:27]3[CH2:30][C@H:29]([CH2:31][N:44]4[CH2:50][CH2:49][CH2:48][C@@H:45]4[CH2:46][OH:47])[CH2:28]3)[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

4

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 2724541Prolinol, (R)-HCID 178435367HCID 178435367, compound

Product 1

HCID 178435364HCID 178435364, compound

Procedure

The title compound is prepared in analogy to Example 116 from cis-{3-[4-amino-5-(3-benzoyloxy-phenyl)-6-ethyl-pyrrolo[2,3-d]pyrimidin-7-yl]-cyclobutyl}-methanol of Example 124, p-toluenesulfonyl chloride and D-prolinol (Fluka, Buchs, Switzerland). Analytical HPLC-MS: tR=1.48 min; ES-MS: m/eo=512.48.

Sources & evidence

ORD record
ord-5ccc241c184a40d49160584b14fd0450
Source dataset
uspto-grants-2008_02
Patent number
US07326699B2

Reaction notes

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