HuagongsheHuagongshe Chemistry Print Report · For research reference only
Formaldehyde → N-(4-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-propylmethanesulfonamide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Formaldehyde | HCID 712 | — |
| Reactant | Trifluoroacetic acid | HCID 6422 | — |
| Reactant | Sodium triacetoxyborohydride | HCID 5049666 | — |
| Reactant | N-(4-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-6-{benzyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-propylmethanesulfonamide | HCID 11467174 | — |
| Reactant | Methyl[(2-methylcyclopropyl)methyl]amine | HCID 43163690 | — |
| Reactant | Tert-butyl [1-benzyl-2-({2-chloro-6-[(methylsulfonyl)(propyl)amino]pyridin-4-yl}methoxy)-1-methylethyl]carbamate | HCID 58856338 | — |
| Solvent | Ethanol | HCID 702 | — |
| Solvent | Dichloroethane methanol | HCID 22036585 | — |
| Product | N-(4-[(2-amino-2-methyl-3-phenylpropoxy)methyl]-6-{methyl[(2-methylcyclopropyl)methyl]amino}pyridin-2-yl)-N-propylmethanesulfonamide | HCID 11225561 | — |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07354942B2 |
| Source dataset | uspto-grants-2008_04 |
| ORD ID | ord-ef45835c7d5e417d8e4b4347bb56fe41 |
| Source note | uspto-grants-2008_04 |