Diisopropylethylamine → tert-butyl-N-{1-[(6-amino-4-chloropyridin-2-yl)carbamoyl]ethyl}carbamate

HRID 1772164

Reaction equation

HRID 1772164 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([O:29][C:30]([NH:32][CH:33]([CH3:37])[C:34]([OH:36])=O)=[O:31])([CH3:28])([CH3:27])[CH3:26].[Cl:38][C:39]1[CH:44]=[C:43]([NH2:45])[N:42]=[C:41]([NH2:46])[CH:40]=1.CCN(C(C)C)C(C)C>CN1C(=O)CCC1>[C:25]([O:29][C:30](=[O:31])[NH:32][CH:33]([C:34](=[O:36])[NH:46][C:41]1[CH:40]=[C:39]([Cl:38])[CH:44]=[C:43]([NH2:45])[N:42]=1)[CH3:37])([CH3:26])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2378474-Chloropyridine-2,6-diamineHCID 2684712-N-Boc-aminopropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 117903116tert-butyl-N-{1-[(6-amino-4-chloropyridin-2-yl)carbamoyl]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

HATU (2.7 g, 7.1 mmol) is added to a mixture of 2-{[(tert-butoxy)carbonyl]amino}-propanoic acid (850 mg, 4.5 mmol), 4-chloropyridine-2,6-diamine (1 g, 7.0 mmol), DIPEA (4.6 ml, 26.5 mmol) and NMP (7 ml) and the mixture is stirred at RT for 18 h. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 770 mg (55%). HPLC-MS: M+H=315 (Method—2).

Workup

  1. concentrationThe mixture is concentrated in vacuo
  2. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-84646cea1bb54e5da6bbe6b6fb421cdc
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Linked notes

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