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

HRID 899470Notes

Reaction equation

HRID 899470 reaction equation
C(C(NC(=O)OC(C)(C)C)(C)COCC1C=C(N(S(C)(=O)=O)CCC)N=C(Cl)C=1)C1C=CC=CC=1.CNCC1CC1C.C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(C(F)(F)F)=O.[NH2:66][C:67]([CH3:105])([CH2:98][C:99]1[CH:104]=[CH:103][CH:102]=[CH:101][CH:100]=1)[CH2:68][O:69][CH2:70][C:71]1[CH:76]=[C:75]([N:77]([CH2:83]C2C=CC=CC=2)[CH2:78][CH:79]2[CH2:81][CH:80]2[CH3:82])[N:74]=[C:73]([N:90]([CH2:95][CH2:96][CH3:97])[S:91]([CH3:94])(=[O:93])=[O:92])[CH:72]=1>ClC(Cl)C.CO.CCO>[NH2:66][C:67]([CH3:105])([CH2:98][C:99]1[CH:100]=[CH:101][CH:102]=[CH:103][CH:104]=1)[CH2:68][O:69][CH2:70][C:71]1[CH:76]=[C:75]([N:77]([CH3:83])[CH2:78][CH:79]2[CH2:81][CH:80]2[CH3:82])[N:74]=[C:73]([N:90]([CH2:95][CH2:96][CH3:97])[S:91]([CH3:94])(=[O:92])=[O:93])[CH:72]=1

Participants

9

Reactant 6

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 11467174N-(4-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-6-{benzyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-propylmethanesulfonamideHCID 43163690Methyl[(2-methylcyclopropyl)methyl]amine2×HCID 58856338Tert-butyl [1-benzyl-2-({2-chloro-6-[(methylsulfonyl)(propyl)amino]pyridin-4-yl}methoxy)-1-methylethyl]carbamate

Product 1

HCID 11225561N-(4-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-propylmethanesulfonamide

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 22036585Dichloroethane methanolSolvent

Procedure

N-(4-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-propylmethanesulfonamide was prepared from intermediate VI and N-methyl-1-(2-methylcyclopropyl)methanamine (prepared from intermediate V) by methylation with formaldehyde in dichloroethane/methanol, in the presence of NaBH(OAc)3, followed 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 C26H40N4O3S: 489.2893, found: 489.2891.

Sources & evidence

ORD record
ord-ef45835c7d5e417d8e4b4347bb56fe41
Source dataset
uspto-grants-2008_04
Patent number
US07354942B2

Reaction notes

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