Triethylamine → HCID 178523411, compound

HRID 456634Notes

Reaction equation

HRID 456634 reaction equation
C(N(CC)CC)C.[NH:8]1[C:12]2=[N:13][CH:14]=[CH:15][CH:16]=[C:11]2[C:10]([C:17]2[NH:21][CH:20]=[C:19]([C:22]([OH:24])=O)[CH:18]=2)=[N:9]1.[NH2:25][CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.C(P(=O)(OCC)OCC)#N>C(#N)C.CN(C=O)C.C(Cl)Cl>[N:28]1([CH2:27][CH2:26][NH:25][C:22]([C:19]2[CH:18]=[C:17]([C:10]3[C:11]4[C:12](=[N:13][CH:14]=[CH:15][CH:16]=4)[NH:8][N:9]=3)[NH:21][CH:20]=2)=[O:24])[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 4082852-MorpholinoethylamineHCID 178524798HCID 178524798, compound

Product 1

HCID 178523411HCID 178523411, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.073 mL) was added to a mixture of 5-(1H-pyrazolo[3,4-b]pyridin-3-yl)-1H-pyrrole-3-carboxylic acid (100 mg, 0.44 mmol) (from Example 12) and 4-(2-aminoethyl)morpholine (62.8 mg, 1.1 eq.) (Aldrich, Milwaukee, Wis.) in acetonitrile (1 mL) and DMF (1 mL). The mixture was cooled in an ice bath and to it was added diethyl cyanophosphonate (86 mg, 1.2 eq.). The mixture was allowed to warm up slowly to room temperature and stirred for overnight. The reaction was diluted with DCM, washed with NaHCO3 and water, dried and concentrated. The residue was purified on a silica gel column to give the titled compound.

Workup

  1. temperatureThe mixture was cooled in an ice bath and to it
  2. washwashed with NaHCO3 and water
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified on a silica gel column

Sources & evidence

ORD record
ord-db9b95f53a6c44f28b765ebd6a0c7c3b
Source dataset
uspto-grants-2007_03
Patent number
US07186716B2

Reaction notes

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