HCID 21471626, compound → HCID 58933876, compound

HRID 854312Notes

Reaction equation

HRID 854312 reaction equation
[C:1]1([CH2:7][CH2:8][S:9]([N:12]2[CH2:17][CH2:16][CH:15]([CH2:18][NH2:19])[CH2:14][CH2:13]2)(=[O:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:20]([O:24][C:25]([NH:27][C:28]1[N:33]=[CH:32][C:31]([C:34](O)=[O:35])=[CH:30][N:29]=1)=[O:26])([CH3:23])([CH3:22])[CH3:21]>>[C:20]([O:24][C:25](=[O:26])[NH:27][C:28]1[N:33]=[CH:32][C:31]([C:34](=[O:35])[NH:19][CH2:18][CH:15]2[CH2:14][CH2:13][N:12]([S:9]([CH2:8][CH2:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:10])=[O:11])[CH2:17][CH2:16]2)=[CH:30][N:29]=1)([CH3:23])([CH3:21])[CH3:22]

Participants

3

Reactant 2

HCID 21471626HCID 21471626, compoundHCID 22135729[1-(2-Phenylethylsulfonyl)piperidin-4-yl]methanamine

Product 1

HCID 58933876HCID 58933876, compound

Procedure

(5-{[1-(2-Phenyl-ethanesulfonyl)-piperidin-4-ylmethyl]-carbamoyl}-pyrimidin-2-yl)-carbamic acid tert-butyl ester was prepared from C-[1-(2-phenyl-ethanesulfonyl)-piperidin-4-yl]-methylamine and 2-tert-butoxycarbonylamino-pyrimidine-5-carboxylic acid (prepared by BOC protection of ethyl 2-amino-5-pyrimidine carboxylate [prepared as described by P. Schenone, et al., J. Heterocyclic Chem., 27:295–305(1990)] using di-tert-butyl dicarbonate and 4-dimethylaminopyridine in acetonitrile, followed by saponification with sodium hydroxide and neutralization with dilute aqueous HCl) as described in EXAMPLE 1, Step 2:

Sources & evidence

ORD record
ord-573705340d2f4e6889962c636a247862
Source dataset
uspto-grants-2007_08
Patent number
US07259157B2

Reaction notes

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