Dicyclohexylcarbodiimide → tert-butyl-N-[1-[[5-[benzenesulfonyl(methyl)amino]-6-(2-phenylethynyl)-pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate

HRID 535437Notes

Reaction equation

HRID 535437 reaction equation
[CH3:1][N:2]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:3]([CH3:7])[C:4]([OH:6])=O.C1(N=C=NC2CCCCC2)CCCCC1.[NH2:30][C:31]1[N:36]=[C:35]([C:37]#[C:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)[C:34]([N:45]([CH3:55])[S:46]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)(=[O:48])=[O:47])=[CH:33][CH:32]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[C:11]([O:10][C:8](=[O:9])[N:2]([CH:3]([CH3:7])[C:4]([NH:30][C:31]1[CH:32]=[CH:33][C:34]([N:45]([S:46]([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)(=[O:48])=[O:47])[CH3:55])=[C:35]([C:37]#[C:38][C:39]2[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=2)[N:36]=1)=[O:6])[CH3:1])([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 44368572-(((Tert-butoxy)carbonyl)(methyl)amino)propanoic acidHCID 86694389N-[6-amino-2-(2-phenylethynyl)pyridin-3-yl]-N-methylbenzenesulfonamide

Product 1

HCID 86694427tert-butyl-N-[1-[[5-[benzenesulfonyl(methyl)amino]-6-(2-phenylethynyl)-pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 2-[methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoic acid (54 mg, 0.26 mmol) and N,N′-dicyclohexylcarbodiimide (27 mg, 0.13 mmol) in DCM (1.5 ml) is stirred at RT for 20 minutes. This mixture is added to N-[6-amino-2-(2-phenylethynyl)pyridin-3-yl]-N-methylbenzenesulfonamide E5a (16 mg, 0.04 mmol) and DIPEA (9 μl; 0.05 mmol) in DCM (0.5 ml). After stirring for 4 days at 40° C. the reaction mixture is diluted with DCM and extracted with water. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The crude product (22 mg) is used in the next step without further purification.

Workup

  1. stirringAfter stirring for 4 days at 40° C. the reaction mixture
  2. extractionextracted with water
  3. dry with materialThe combined organic layers are dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product (22 mg) is used in the next step without further purification

Sources & evidence

ORD record
ord-3c65ac84661a465ca3e3fd404214d0a6
Source dataset
uspto-grants-2014_10
Patent number
US08859541B2

Reaction notes

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