1,2-Dichloroethane → N-[4-(4-{2-[1-(N,N-dimethylglycyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1-ethyl-1H-pyrazol-3-yl)phenyl]-N'-phenylurea

HRID 1727722

Reaction equation

HRID 1727722 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]3[NH:14][C:15]([C:17]4[CH2:18][CH2:19][NH:20][CH2:21][CH:22]=4)=[CH:16][C:9]=23)[C:5]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:32][C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=3)=[O:31])=[CH:25][CH:24]=2)=[N:4]1)[CH3:2].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.[CH3:60][N:61]([CH3:66])[CH2:62][C:63](O)=[O:64]>CN(C)C=O.C(OCC)(=O)C>[CH3:60][N:61]([CH3:66])[CH2:62][C:63]([N:20]1[CH2:19][CH:18]=[C:17]([C:15]2[NH:14][C:10]3=[N:11][CH:12]=[CH:13][C:8]([C:6]4[C:5]([C:23]5[CH:28]=[CH:27][C:26]([NH:29][C:30]([NH:32][C:33]6[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=6)=[O:31])=[CH:25][CH:24]=5)=[N:4][N:3]([CH2:1][CH3:2])[CH:7]=4)=[C:9]3[CH:16]=2)[CH2:22][CH2:21]1)=[O:64]

Participants

8

Reactant 5

HCID 111,2-DichloroethaneHCID 673N,N-DimethylglycineHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 58980124N-(4-{1-ethyl-4-[2-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)-N'-phenylurea

Product 1

HCID 58980076N-[4-(4-{2-[1-(N,N-dimethylglycyl)-1,2,3,6-tetrahydro-4-pyridinyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}-1-ethyl-1H-pyrazol-3-yl)phenyl]-N'-phenylurea

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(4-{1-ethyl-4-[2-(1,2,3,6-tetrahydro-4-pyridinyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-1H-pyrazol-3-yl}phenyl)-N′-phenylurea (0.23 mmol) was in N,N-dimethylformamide (3.0 mL) was added EDC (0.39 mmol), HOBt (0.39 mmol), triethylamine (1.38 mmol) followed by N,N dimethylglycine (0.39 mmol). The reaction stirred at room temp for 16 h. The reaction was poured into ethyl acetate and washed saturated sodium bicarbonate (2×10 mL). The organic layer was evaporated and purification of the residue by Gilson reverse phase HPLC provided the title product. ESMS [M+H]+: 589.4

Workup

  1. washwashed saturated sodium bicarbonate (2×10 mL)
  2. customThe organic layer was evaporated
  3. custompurification of the residue by Gilson reverse phase HPLC

Sources & evidence

ORD record
ord-e81ec8941d324dbfa7cb54891118b7a1
Source dataset
uspto-grants-2009_02
Patent number
US07495102B2

Linked notes

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