1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 68513145, compound

HRID 2241265Notes

Reaction equation

HRID 2241265 reaction equation
[CH3:1][O:2][C:3]1[CH:28]=[CH:27][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16]([O:17][C:18]4[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=4[F:25])=[C:11]3[C:10]([I:26])=[N:9]2)=[CH:5][CH:4]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33]([N:36]2[C:41](=[O:42])[C:40]([C:43](O)=[O:44])=[CH:39][CH:38]=[N:37]2)=[CH:32][CH:31]=1.C1C=CC2N(O)N=NC=2C=1.O.CCN=C=NCCCN(C)C>CN(C=O)C>[F:25][C:19]1[CH:20]=[C:21]([NH:24][C:43]([C:40]2[C:41](=[O:42])[N:36]([C:33]3[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=3)[N:37]=[CH:38][CH:39]=2)=[O:44])[CH:22]=[CH:23][C:18]=1[O:17][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[N:8]([CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:28][CH:27]=3)[N:9]=[C:10]([I:26])[C:11]=12

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 667671712-(4-Fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acidHCID 672210033-Fluoro-4-((3-iodo-1-(4-methoxybenzyl)-1H-pyrazolo[3,4-b]pyridin-4-yl)oxy)aniline

Product 1

HCID 68513145HCID 68513145, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 4-(1-(4-methoxybenzyl)-3-iodo-1H-pyrazolo[3,4-b]pyridin-4-yloxy)-3-fluorobenzenamine (1.50 g, 3.06 mmol; prepared as in Example 7, Step B), 2-(4-fluorophenyl)-3-oxo-2,3-dihydropyridazine-4-carboxylic acid (1.43 g, 6.12 mmol; prepared as in Example 19, Step C), and HOBT-H2O (2.81 g, 18.4 mmol) dissolved in dry DMF (30 mL) was added EDCI (3.52 g, 18.4 mmol). The mixture was stirred at room temperature for 3 hours. The reaction mixture was then partitioned between ethyl acetate (60 mL) and aqueous NH4Cl (100 mL). The organic layer was separated, washed with saturated NaHCO3, dried over NaSO4, and evaporated to dryness. The crude material was triturated with MeOH and the solid removed by filtration, dried to afford the title compound as yellow solid. Yield: 1.93 g, 89%. LRMS (APCI pos) m/e 707.0 (M+H).

Workup

  1. customThe reaction mixture was then partitioned between ethyl acetate (60 mL) and aqueous NH4Cl (100 mL)
  2. customThe organic layer was separated
  3. washwashed with saturated NaHCO3
  4. dry with materialdried over NaSO4
  5. customevaporated to dryness
  6. customThe crude material was triturated with MeOH
  7. customthe solid removed by filtration
  8. customdried

Sources & evidence

ORD record
ord-9cb7226615cd40b0ada251d7740eed8f
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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