Cyclopropylamine → 4-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamide

HRID 737169Notes

Reaction equation

HRID 737169 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[N:6]=1.CN(C(ON1N=NC2[CH:27]=[CH:28][CH:29]=[N:30]C1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.C1(N)CC1>CN(C=O)C.O>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([NH:30][CH:29]3[CH2:27][CH2:28]3)=[O:13])=[CH:14][CH:15]=2)[N:6]=1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 6131794-(2-Amino-1,3-thiazol-4-yl)benzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 592287924-(2-Amino-thiazol-4-yl)-N-cyclopropyl-benzamideYield 95%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

4-(2-Amino-thiazol-4-yl)-benzoic acid (4.4 g, 20 mmol) was dissolved in DMF (100 mL) and treated with HATU (1.1 eq. 8.4 g) and DIEA (2.1 eq, 7.5 mL) and stirred for 15 minutes. Then cyclopropyl amine (1.1 eq, 1.5 mL) was added and the mixture stirred at ambient temperature for 1 hr. The reaction was diluted with 100 mL of water, extracted with EtOAc (3×100 mL) dried with brine (100 mL) and then Na2SO4 and the solvents removed. The resulting solid was triturated with ether to give the product >95% purity by HPLC. MS: 260.3 (M+H).

Workup

  1. stirringthe mixture stirred at ambient temperature for 1 hr
  2. extractionextracted with EtOAc (3×100 mL)
  3. dry with materialdried with brine (100 mL)
  4. customNa2SO4 and the solvents removed
  5. customThe resulting solid was triturated with ether

Sources & evidence

ORD record
ord-2df0e55deaa9479ebeb51b0192092a6d
Source dataset
uspto-grants-2009_09
Patent number
US07595398B2

Reaction notes

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