Water → But-2-ynoic acid (2-{6-[3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-ureido]-pyrimidin-4-ylamino}-phenyl)-amide

HRID 58160Notes

Reaction equation

HRID 58160 reaction equation
C(OC(=O)[N:7]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[NH2:45])[C:8]1[CH:13]=[C:12]([N:14]([CH3:38])[C:15]([N:17]([C:26]2[C:31]([Cl:32])=[C:30]([O:33][CH3:34])[CH:29]=[C:28]([O:35][CH3:36])[C:27]=2[Cl:37])COCC[Si](C)(C)C)=[O:16])[N:11]=[CH:10][N:9]=1)(C)(C)C.C1CCC(N=C=NC2CCCCC2)CC1.[C:62](O)(=[O:66])[C:63]#[C:64][CH3:65].O>C(Cl)Cl>[Cl:37][C:27]1[C:28]([O:35][CH3:36])=[CH:29][C:30]([O:33][CH3:34])=[C:31]([Cl:32])[C:26]=1[NH:17][C:15](=[O:16])[N:14]([C:12]1[N:11]=[CH:10][N:9]=[C:8]([NH:7][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=2[NH:45][C:62](=[O:66])[C:63]#[C:64][CH3:65])[CH:13]=1)[CH3:38]

Participants

6

Reactant 4

HCID 962WaterHCID 10868DicyclohexylcarbodiimideHCID 685352-Butynoic acidHCID 131736978(2-Amino-phenyl)-{6-[3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-ureido]-pyrimidin-4-yl}-carbamic acid tert-butyl ester

Product 1

HCID 118029145But-2-ynoic acid (2-{6-[3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-ureido]-pyrimidin-4-ylamino}-phenyl)-amideYield 50.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of (2-amino-phenyl)-{6-[3-(2,6-dichloro-3,5-dimethoxy-phenyl)-1-methyl-3-(2-trimethylsilanyl-ethoxymethyl)-ureido]-pyrimidin-4-yl}-carbamic acid tert-butyl ester (50 g, 0.075 mmol) and DCC (42 g, 0.2 mmol) in DCM (50 mL) was added a solution of but-2-ynoic acid (13 g, 0.15 mmol) in DCM (10 mL) at 0° C., and the resulting mixture was stirred at room temperature overnight. Water (1 mL) was added to quench the reaction. The mixture was concentrated and the residue was purified by reverse phase chromatography to obtain the title compound (20 mg, yield: 34%). MS (ESI): 659 [M+H]+.

Workup

  1. customto quench
  2. customthe reaction
  3. concentrationThe mixture was concentrated
  4. customthe residue was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-0795b596c5a64f4eb8c95eb2bdddb6ac
Source dataset
uspto-grants-2016_09
Patent number
US09434697B2

Reaction notes

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