Cyclopropylamine → HCID 24829801, compound

HRID 2245942Notes

Reaction equation

HRID 2245942 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2([C:12]3[N:16]4[N:17]=[C:18]([C:21]5[CH:29]=[CH:28][C:24]([C:25](O)=[O:26])=[CH:23][CH:22]=5)[CH:19]=[N:20][C:15]4=[N:14][N:13]=3)[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[CH:30]1([NH2:33])[CH2:32][CH2:31]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.C(N(CC)C(C)C)(C)C>CN(C=O)C.CO>[CH:30]1([NH:33][C:25](=[O:26])[C:24]2[CH:28]=[CH:29][C:21]([C:18]3[CH:19]=[N:20][C:15]4[N:16]([C:12]([C:9]5([C:6]6[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=6)[CH2:10][CH2:11]5)=[N:13][N:14]=4)[N:17]=3)=[CH:22][CH:23]=2)[CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 59216350HCID 59216350, compound

Product 1

HCID 24829801HCID 24829801, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-{3-[1-(4-methoxyphenyl)cyclopropyl][1,2,4]triazolo[4,3-b][1,2,4]triazin-6-yl}benzoic acid (isomer-I from step 2, 14.0 mg, 0.0361 mmol), cyclopropylamine (3.76 μL, 0.0542 mmol), benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (16.0 mg, 0.0361 mmol) and N,N-diisopropylethylamine (25.2 μL, 0.145 mmol) in DMF (1.0 mL) was stirred at RT for 3 h. The mixture was diluted with methanol and purified by RP-HPLC (pH=10) to give the desired product. Analytical LCMS: (M+H)+=427.3.

Workup

  1. custompurified by RP-HPLC (pH=10)

Sources & evidence

ORD record
ord-f6c4848620224dc8bf3153220906b936
Source dataset
uspto-grants-2010_03
Patent number
US07683060B2

Reaction notes

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