Tert-butyl (piperidin-4-ylmethyl)carbamate → Tert-butyl (1-(2-chlorofuro[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate

HRID 1038795Notes

Reaction equation

HRID 1038795 reaction equation
S(C1C=CC(N[C:12]2[N:13]=[C:14]([N:21]3[CH2:26][CH2:25][CH:24]([CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:23][CH2:22]3)[C:15]3[O:20][CH:19]=[CH:18][C:16]=3[N:17]=2)=CC=1)(=O)(=O)N.[Cl:36]C1N=C(Cl)C2OC=CC=2N=1.N1CCC(CNC(=O)OC(C)(C)C)CC1>>[Cl:36][C:12]1[N:13]=[C:14]([N:21]2[CH2:22][CH2:23][CH:24]([CH2:27][NH:28][C:29](=[O:35])[O:30][C:31]([CH3:34])([CH3:32])[CH3:33])[CH2:25][CH2:26]2)[C:15]2[O:20][CH:19]=[CH:18][C:16]=2[N:17]=1

Participants

4

Reactant 3

HCID 723429Tert-butyl (piperidin-4-ylmethyl)carbamateHCID 457899682,4-Dichlorofuro[3,2-D]pyrimidineHCID 70143000Tert-butyl(1-(2-(4-sulfamoylphenylamino)furo[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate

Product 1

HCID 86665090Tert-butyl (1-(2-chlorofuro[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate

Procedure

The precursor to Example #C.1, tert-butyl (1-(2-(4-sulfamoylphenylamino)furo[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate, was prepared as shown in Scheme B. 2,4-Dichlorofuro[3,2-d]pyrimidine [Ark Pharm] and tert-butyl piperidin-4-ylmethylcarbamate [Astatech] are reacted following conditions given in General Procedure A to give tert-butyl (1-(2-chlorofuro[3,2-d]pyrimidin-4-yl)piperidin-4-yl)methylcarbamate. The intermediate is then reacted with 4-aminobenzenesulfonamide using the conditions described in General Procedure B to give the precursor to Example #C.1. The reaction sequence detailed above is translated in the preparations and examples section to “prepared using A from 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] with tert-butyl piperidin-4-ylmethylcarbamate [Astatech] and B with 4-aminobenzenesulfonamide.”

Sources & evidence

ORD record
ord-d6c016dc052f4821b828c589137ce415
Source dataset
uspto-grants-2013_10
Patent number
US08551981B2

Reaction notes

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