Methylamine → HCID 86694423, compound

HRID 535432Notes

Reaction equation

HRID 535432 reaction equation
Br[CH:2]([CH3:6])[C:3](Br)=[O:4].[C:7]1([C:13]#[C:14][C:15]2[N:20]=[C:19]([NH2:21])[CH:18]=[C:17]([C:22]([F:25])([F:24])[F:23])[C:16]=2[C:26]2[CH:27]=[N:28][CH:29]=[N:30][CH:31]=2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:32]([N:34](CC)CC)C.CN>CN(C1C=CN=CC=1)C.O1CCOCC1>[CH3:32][NH:34][CH:2]([CH3:6])[C:3]([NH:21][C:19]1[CH:18]=[C:17]([C:22]([F:25])([F:23])[F:24])[C:16]([C:26]2[CH:27]=[N:28][CH:29]=[N:30][CH:31]=2)=[C:15]([C:14]#[C:13][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:20]=1)=[O:4]

Participants

7

Reactant 4

HCID 6329MethylamineHCID 8471TriethylamineHCID 79047Propanoyl bromide, 2-bromo-HCID 86694424HCID 86694424, compound

Product 1

HCID 86694423HCID 86694423, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

Under stirring at 0° C. 2-bromopropanoyl bromide (44 μl, 0.42 mmol) is added dropwise to a mixture of 6-(2-phenylethynyl)-5-pyrimidin-5-yl-4-(trifluoromethyl)pyridin-2-amine C3d (95 mg, 0.28 mmol), triethylamine (59 μl, 0.42 mmol), DMAP (0.3 mg, 3 μmol) and dioxane (1.4 ml). The mixture is warmed to RT and stirred for 1 h. Methylamine (solution in THF 2 mol/l, 1.4 ml, 2.8 mmol) is added and stirring continued for 6 h. The mixture is concentrated in vacuo and the product purified by RP HPLC. Yield: 45 mg (38%). HPLC-MS: M+H=426; tR=1.27 min (*Method—1).

Workup

  1. temperatureThe mixture is warmed to RT
  2. stirringstirred for 1 h
  3. stirringstirring
  4. concentrationThe mixture is concentrated in vacuo
  5. customthe product purified by RP HPLC

Sources & evidence

ORD record
ord-d989ee46c12f4dad89586f3809ddccfb
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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