Triethylamine → HCID 136121570, compound

HRID 2062203Notes

Reaction equation

HRID 2062203 reaction equation
[CH3:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([N:19]3[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]3)=[N:7][C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])=[N:9]2)=[CH:4][CH:3]=1.[OH:25][C@@H:26]([CH2:30][C:31]1[NH:35][CH:34]=[N:33][CH:32]=1)[C:27](O)=[O:28].C(N(CC)CC)C.F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1>C(Cl)Cl.O>[OH:25][C@@H:26]([CH2:30][C:31]1[NH:35][CH:34]=[N:33][CH:32]=1)[C:27]([N:22]1[CH2:23][CH2:24][N:19]([C:6]2[C:5]3[C:10](=[CH:11][C:2]([CH3:1])=[CH:3][CH:4]=3)[N:9]=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[OH:18])[N:7]=2)[CH2:20][CH2:21]1)=[O:28]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 440129(S)-2-hydroxy-3-(1H-imidazol-4-yl)propanoic acidHCID 1361346166-[7-methyl-4-(1-piperazinyl)-1H-quinazolin-2-ylidene]-1-cyclohexa-2,4-dienone

Product 1

HCID 136121570HCID 136121570, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

2-(7-Methyl-4-(piperazin-1-yl)quinazolin-2-yl)phenol (87 mg, 0.27 mmol), (S)-2-hydroxy-3-(1H-imidazol-5-yl)propanoic acid (64 mg, 0.41 mmol), triethylamine (76 μL, 0.54 mmol), and BOP (180 mg, 0.41 mmol) in 1 mL of CH2Cl2 were stirred at room temperature for 1.5 h. The reaction mixture was diluted with H2O and CH2Cl2. The organic layer was dried over Na2SO4 and concentrated. Purification using 1-15% MeOH in CH2Cl2 gave (S)-2-hydroxy-1-(4-(2-(2-hydroxyphenyl)-7-methylquinazolin-4-yl)piperazin-1-yl)-3-(1H-imidazol-5-yl)propan-1-one. LC/MS: m/z 459.3 (M+H)+ at 2.13 min (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA)).

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated
  3. customPurification

Sources & evidence

ORD record
ord-c3fac0dd542747e5a7c3c5a040c03f52
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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