Pyrrolidone carboxylic acid → HCID 136366898, compound

HRID 2062324Notes

Reaction equation

HRID 2062324 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:16]3[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=3)[N:10]=[C:9]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[OH:24])[N:8]=2)[CH2:3]1.C(N(CC)CC)C.[O:32]=[C:33]1[NH:37][CH:36]([C:38](O)=[O:39])[CH2:35][CH2:34]1.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>O.C(Cl)Cl>[OH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:9]1[N:8]=[C:7]([N:4]2[CH2:5][CH2:6][CH:2]([NH:1][C:38]([C@H:36]3[CH2:35][CH2:34][C:33](=[O:32])[NH:37]3)=[O:39])[CH2:3]2)[C:16]2[C:11](=[CH:12][C:13]([CH3:17])=[CH:14][CH:15]=2)[N:10]=1

Participants

7

Reactant 4

HCID 499Pyrrolidone carboxylic acidHCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 136121376(R)-2-(4-(3-aminopyrrolidin-1-yl)-7-methylquinazolin-2-yl)phenol

Product 1

HCID 136366898HCID 136366898, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To (R)-2-[4-(3-amino-pyrrolidin-1-yl)-7-methyl-quinazolin-2-yl]-phenol (71 mg, 0.22 mmol) was added 890 μL of CH2Cl2. To this solution was added sequentially triethylamine (47 μL, 0.34 mmol) and 5-oxo-pyrrolidine-2-carboxylic acid (34.8 mg, 0.27 mmol) and BOP (119 mg, 0.27 mmol). The reaction mixture was stirred at room temperature for 2 h and diluted with water and CH2Cl2 (10 mL). The organic layer was separated and dried over Na2SO4, and the solvent was removed under reduced pressure to give (R)-5-oxo-pyrrolidine-2-carboxylic acid {1-[2-(2-hydroxy-phenyl)-7-methyl-quinazolin-4-yl]-pyrrolidin-3-yl}-amide. LC/MS: m/z 432.5 (M+H)+ at 2.24 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-fd7e0a5091e94afc95b3bc6320782a29
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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