1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68290560, compound

HRID 68902Notes

Reaction equation

HRID 68902 reaction equation
CN(C)CCCN=C=NCC.[Cl:12][C:13]1[CH:14]=[N:15][C:16]([N:19]2[CH2:24][CH2:23][CH:22]([NH:25][CH:26]3[CH2:28][CH2:27]3)[CH2:21][CH2:20]2)=[N:17][CH:18]=1.[CH3:29][C:30]1[N:31]([C:35]2[CH:43]=[CH:42][C:38]([C:39](O)=[O:40])=[CH:37][CH:36]=2)[CH:32]=[CH:33][N:34]=1.ON1C2C=CC=CC=2N=N1.C(#N)C.O.FC(F)(F)C(O)=O>CN(C)C=O.C(N(CC)CC)C>[Cl:12][C:13]1[CH:14]=[N:15][C:16]([N:19]2[CH2:24][CH2:23][CH:22]([N:25]([CH:26]3[CH2:28][CH2:27]3)[C:39](=[O:40])[C:38]3[CH:37]=[CH:36][C:35]([N:31]4[CH:32]=[CH:33][N:34]=[C:30]4[CH3:29])=[CH:43][CH:42]=3)[CH2:21][CH2:20]2)=[N:17][CH:18]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 138159884-(2-methyl-1H-imidazol-1-yl)benzoic acidHCID 22145617Water TFA acetonitrileHCID 682895731-(5-chloropyrimidin-2-yl)-N-cyclopropylpiperidin-4-amine

Product 1

HCID 68290560HCID 68290560, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8471TriethylamineSolvent

Procedure

1-(3-Dimethylamino-propyl)-3-ethyl-carbodiimide (EDC, 12 mg) in N,N-dimethylformamide (0.1 mL) is added to a solution of [1-(5-chloro-pyrimidin-2-yl)-piperidin-4-yl]-cyclopropyl-amine (5 mg), 4-(2-methyl-imidazol-1-yl)-benzoic acid (6 mg), 1-hydroxy-benzo-triazole (3 mg), and triethylamine (15 μL) in N,N-dimethylformamide (0.4 mL) at room temperature. The solution is stirred for 18 h and then submitted to chromatography on reversed phase (HPLC, acetonitrile/water/trifluoroacetic acid) to give the pure title compound. LC (method 19): tR=3.97 min; Mass spectrum (ESI+): m/z=437 [M+H]+.

Sources & evidence

ORD record
ord-931b37d612b54daeb113ad35abece5a9
Source dataset
uspto-grants-2014_09
Patent number
US08822471B2

Reaction notes

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