Sodium Bicarbonate → 2-(methylamino)-N-[5-(2-methylimidazo[1,2-a]pyridin-3-yl)-6-[2-(1-methyl-2-oxoquinolin-6-yl)ethynyl]pyridin-2-yl]propanamide

HRID 535411Notes

Reaction equation

HRID 535411 reaction equation
C(O[C:6](=O)[N:7](C)[CH:8]([CH3:42])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]3=[N:20][C:19]=2[CH3:27])=[C:14]([C:28]#[C:29][C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[N:36]([CH3:40])[C:35](=[O:41])[CH:34]=[CH:33]3)[N:13]=1)=[O:10])(C)(C)C.C(Cl)Cl.C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:6][NH:7][CH:8]([CH3:42])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:22]3[CH:23]=[CH:24][CH:25]=[CH:26][C:21]3=[N:20][C:19]=2[CH3:27])=[C:14]([C:28]#[C:29][C:30]2[CH:31]=[C:32]3[C:37](=[CH:38][CH:39]=2)[N:36]([CH3:40])[C:35](=[O:41])[CH:34]=[CH:33]3)[N:13]=1)=[O:10]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 86694397tert-butyl-N-methyl-N-[1-[[5-(2-methylimidazo[1,2-a]pyridin-3-yl)-6-[2-(1-methyl-2-oxoquinolin-6-yl)ethynyl]pyridin-2-yl]amino]-1-oxopropan-2-yl]-carbamate

Product 1

HCID 717148342-(methylamino)-N-[5-(2-methylimidazo[1,2-a]pyridin-3-yl)-6-[2-(1-methyl-2-oxoquinolin-6-yl)ethynyl]pyridin-2-yl]propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of tert-butyl-N-methyl-N-[1-[[5-(2-methylimidazo[1,2-a]pyridin-3-yl)-6-[2-(1-methyl-2-oxoquinolin-6-yl)ethynyl]pyridin-2-yl]amino]-1-oxopropan-2-yl]carbamate G1b (17 mg, 0.03 mmol) and DCM:TFA (9:1, 2 ml) is stirred at RT for 2 h. The mixture is diluted with DCM and a saturated aqueous solution of NaHCO3 is added. The mixture is extracted with DCM. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 14 mg (99%). HPLC-MS: M+H=491; tR=0.97 min (*Method—1).

Workup

  1. extractionThe mixture is extracted with DCM
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-e1836cd74f4f4fe6bfe5556cc47dbd4f
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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