Diisopropylethylamine → HCID 117706769, compound

HRID 1778543Notes

Reaction equation

HRID 1778543 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C:14]([C:15]([O-:17])=[O:16])=[C:13]([CH2:18]Br)[NH:12][C:11]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[N:10]1.[O:25]=[C:26]1[N:33](C(OC(C)(C)C)=O)[CH2:32][CH:31]2[NH:41][CH:27]1[CH2:28][O:29][CH2:30]2.[CH3:42]CN(C(C)C)C(C)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C:14]([C:15]([O:17][CH3:42])=[O:16])=[C:13]([CH2:18][N:41]2[CH:27]3[C:26](=[O:25])[NH:33][CH2:32][CH:31]2[CH2:30][O:29][CH2:28]3)[NH:12][C:11]([C:20]2[S:21][CH:22]=[CH:23][N:24]=2)=[N:10]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 117697920HCID 117697920, compoundHCID 131734826(4R)-4-(2-chloro-4-fluoro-phenyl)-6-(bromomethyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate2×

Product 1

HCID 117706769HCID 117706769, compoundYield 9.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The titled compound was prepared by following procedure. To a solution of methyl (4R)-6-(bromomethyl)-4-(2-chloro-4-fluoro-phenyl)-2-thiazol-2-yl-1,4-dihydropyrimidine-5-carboxylate (compound C, 0.089 g, 0.20 mmol) and tert-butyl 6-oxo-3-oxa-7,9-diazabicyclo[3.3.1]nonane-7-carboxylate 133a (0.096 g) in CH2Cl2 (3 ml) was added DIPEA (0.2 ml, 1.14 mmol) at room temperature. The resulting mixture was stirred at room temperature overnight. The mixture was concentrated, and the residue (0.120 g, MS: calc'd (MH+) 606, measured (MH+) 606) was dissolved in dichloromethane (3 ml). To it was added trifluoroacetic acid (2 ml) at room temperature. The resulting mixture was stirred at room temperature for 2 hours. Then the mixture was concentrated and the residue was purified by preparative HPLC to give the title compound (10 mg).

Workup

  1. customThe titled compound was prepared
  2. concentrationThe mixture was concentrated
  3. dissolutionthe residue (0.120 g, MS: calc'd (MH+) 606, measured (MH+) 606) was dissolved in dichloromethane (3 ml)
  4. additionTo it was added trifluoroacetic acid (2 ml) at room temperature
  5. stirringThe resulting mixture was stirred at room temperature for 2 hours
  6. concentrationThen the mixture was concentrated
  7. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-26b95c039193404cb56e5c12ba606172
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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