Trifluoroacetic acid → N-(4-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-6-{[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-propylmethanesulfonamide

HRID 899469Notes

Reaction equation

HRID 899469 reaction equation
[CH2:1]([C:8]([NH:28]C(=O)OC(C)(C)C)([CH3:27])[CH2:9][O:10][CH2:11][C:12]1[CH:17]=[C:16]([N:18]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:19][CH2:20][CH3:21])[N:15]=[C:14](Cl)[CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:36][CH:37]1[CH2:39][CH:38]1[CH2:40][NH2:41].C(O)(C(F)(F)F)=O.C(NS(C)(=O)=O)CC>CCO>[NH2:28][C:8]([CH3:27])([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[CH2:9][O:10][CH2:11][C:12]1[CH:13]=[C:14]([NH:41][CH2:40][CH:38]2[CH2:39][CH:37]2[CH3:36])[N:15]=[C:16]([N:18]([CH2:19][CH2:20][CH3:21])[S:22]([CH3:25])(=[O:23])=[O:24])[CH:17]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 235967N-propylmethanesulfonamideHCID 231581082-MethylcyclopropanemethanamineHCID 58856338Tert-butyl [1-benzyl-2-({2-chloro-6-[(methylsulfonyl)(propyl)amino]pyridin-4-yl}methoxy)-1-methylethyl]carbamate

Product 1

HCID 11248510N-(4-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-6-{[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-propylmethanesulfonamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(4-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-6-{[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-propylmethanesulfonamide was prepared from intermediate VI and [(2-methylcyclopropyl)methyl]amine (prepared from N-benzyl-1-(2-trans-methylcyclopropyl)methenamine by hydrogenation on Pd(OH)2, in EtOH, in the presence of TFA), following a similar procedure as described for the preparation of N-4-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-6-{benzyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-propylmethanesulfonamide. HRMS (ES, M+H) calcd. for C25H38N4O3S: 475.2737, found: 475.2719.

Sources & evidence

ORD record
ord-2de08a9ed8564225950b4613a6e94eac
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

Loading…