Diisopropylethylamine → tert-butyl-N-[5-(oxane-4-carbonylamino)-6-(2-phenylethynyl)pyridin-2-yl]-carbamate

HRID 535393Notes

Reaction equation

HRID 535393 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]([OH:9])=O)[CH2:3][CH2:2]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[C:43]([O:47][C:48](=[O:65])[NH:49][C:50]1[CH:55]=[CH:54][C:53]([NH2:56])=[C:52]([C:57]#[C:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[N:51]=1)([CH3:46])([CH3:45])[CH3:44]>CN(C=O)C>[C:43]([O:47][C:48](=[O:65])[NH:49][C:50]1[CH:55]=[CH:54][C:53]([NH:56][C:7]([CH:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[O:9])=[C:52]([C:57]#[C:58][C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)[N:51]=1)([CH3:46])([CH3:44])[CH3:45]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 219302Oxane-4-carboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 86694370tert-butyl-N-[5-amino-6-(2-phenylethynyl)pyridin-2-yl]carbamate

Product 1

HCID 86694378tert-butyl-N-[5-(oxane-4-carbonylamino)-6-(2-phenylethynyl)pyridin-2-yl]-carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of oxane-4-carboxylic acid (45 mg, 0.34 mmol), HATU (162 mg, 0.43 mmol) and DIPEA (43 μl, 0.25 mmol) in DMF (1 ml) is stirred at RT for 30 minutes. Tert-butyl-N-[5-amino-6-(2-phenylethynyl)pyridin-2-yl]carbamate B5a (60 mg, 0.19 mmol) is added and stirring continued for 17 h. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 40 mg (49%). HPLC-MS: M+H=422; tR=1.73 min (*Method—5).

Workup

  1. stirringstirring
  2. waitcontinued for 17 h
  3. concentrationThe mixture is concentrated in vacuo
  4. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-fc3d6d1e172b478bb1707166fb359c69
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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