Diisopropylethylamine → N-(4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-2-(quinazolin-6-ylamino)benzamide

HRID 969690Notes

Reaction equation

HRID 969690 reaction equation
[Li].[N:2]1[C:11]2[C:6](=[CH:7][C:8]([NH:12][C:13]3[CH:21]=[CH:20][CH:19]=[CH:18][C:14]=3[C:15]([OH:17])=O)=[CH:9][CH:10]=2)[CH:5]=[N:4][CH:3]=1.[CH3:22][C:23]1([CH3:34])[C:32]2[C:27](=[CH:28][C:29]([NH2:33])=[CH:30][CH:31]=2)[NH:26][CH2:25][CH2:24]1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C.O>[CH3:22][C:23]1([CH3:34])[C:32]2[C:27](=[CH:28][C:29]([NH:33][C:15](=[O:17])[C:14]3[CH:18]=[CH:19][CH:20]=[CH:21][C:13]=3[NH:12][C:8]3[CH:7]=[C:6]4[C:11](=[CH:10][CH:9]=3)[N:2]=[CH:3][N:4]=[CH:5]4)=[CH:30][CH:31]=2)[NH:26][CH2:25][CH2:24]1

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 3028194LithiumHCID 21961482HCID 21961482, compoundHCID 695118112-(Quinazolin-6-ylamino)-benzoic acid

Product 1

HCID 10342249N-(4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-yl)-2-(quinazolin-6-ylamino)benzamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of the lithium salt of 2-(quinazolin-6-ylamino)-benzoic acid (Step B, 533 mg, 0.72 mmol), 4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-7-ylamine (127 mg, 0.72 mmol), TBTU (462 mg, 1.44 mmol) and DIEA (0.25 mL, 1.44 mmol) in 3 mL of DMF was submitted to microwave irradiation (80° C., 30 min). Water (5 mL) was added to the mixture, and the resultant precipitate was filtered and dried. The crude material was purified with flash chromatography (SiO2, 50% EtOAc/hexane) to afford a white solid. MS (ES+): 424.0 (M+H)+. Calc'd for C26H25N5O: 423.51.

Workup

  1. customwas submitted to microwave irradiation (80° C., 30 min)
  2. filtrationthe resultant precipitate was filtered
  3. customdried
  4. customThe crude material was purified with flash chromatography (SiO2, 50% EtOAc/hexane)
  5. customto afford a white solid

Sources & evidence

ORD record
ord-349fddccf84648ff950a38a4b7c20c2b
Source dataset
uspto-grants-2007_12
Patent number
US07307088B2

Reaction notes

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