Cyclopropylamine → HCID 86591418, compound

HRID 549034Notes

Reaction equation

HRID 549034 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]1[N:11](CC(O)=O)[CH:12]=[CH:13][CH:14]=1.F[P-](F)(F)(F)(F)F.N1([O:35]C(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1.C1(N)CC1.C([N:50]([CH:53]([CH3:55])[CH3:54])[CH2:51][CH3:52])(C)C>CN(C)C=O>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[CH:3]=[C:2]1[C:10]1[N:11]([N:50]([CH:53]2[CH2:54][CH2:55]2)[CH2:51][CH:52]=[O:35])[CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 69828CyclopropylamineHCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 22477497HCID 22477497, compound

Product 1

HCID 86591418HCID 86591418, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A mixture of [2-(1H-pyrrolo[2,3-b]pyridin-2-yl)-pyrrol-1-yl]-acetic acid [10 mg, Example 54] and 2-(1H-benzotriazole-1-yl)1,1,3,3-tetramethyluronium hexafluorophosphate (15.7 mg) in dry dimethylformamide (0.2 mL) was agitated for 1 hour then treated with cyclopropylamine (5.68 μL) and diisopropylethylamine (7.16 μL) in dry dimethylformamide (0.226 mL). After agitating for a further 15 hours the crude mixture was subjected to LC-MS triggered purification affording the title compound. LC-MS: METHOD C: RT=2.44 minutes, 281[M+H]+ and 224 (fragment corresponding to the breaking of the amide bond).

Workup

  1. custompurification

Sources & evidence

ORD record
ord-70132aac64d34b9799fdfe201b84ea41
Source dataset
uspto-grants-2011_05
Patent number
US07943616B2

Reaction notes

Loading…