Water → HCID 178513005, compound

HRID 565370Notes

Reaction equation

HRID 565370 reaction equation
[C:1]1([C:7]2([N:14]3[CH2:19][CH2:18][CH:17]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[N:22]=[C:21]4[NH:29][CH2:30][CH2:31][NH2:32])[CH2:16][CH2:15]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([NH:40][C:41](N1C=CCN1C(=N)NC(OC(C)(C)C)=O)=[NH:42])(OC(C)(C)C)=O.O>C1COCC1>[C:1]1([C:7]2([N:14]3[CH2:15][CH2:16][CH:17]([N:20]4[C:24]5[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=5[N:22]=[C:21]4[NH:29][CH2:30][CH2:31][NH:32][C:41]([NH2:42])=[NH:40])[CH2:18][CH2:19]3)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21268148HCID 21268148, compoundHCID 141617697HCID 141617697, compound

Product 1

HCID 178513005HCID 178513005, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-aminoethylamino-1-[1(1-phenylcycloheptyl)-4-piperidinyl]benzimidazole (Example 27, 85.6 mg, 0.199 mmol) and N, N′-bis Boc guanylpyrazole (117 mg, 0.377 mmol, this was prepared according to the following reported procedure: M. S. Bernatowicz, et al., Tetrahedron Lett., 1993, 34, 3389-3392) in THF (3 ml) was stirred at room temperature for 16 h. Water was added to the reaction mixture and extracted with CH2Cl2. The extracts combined were washed with brine, dried (Na2SO4), filtered, and concentrated. The residue was purified by column chromatography (silica gel: 30 g, hexane/acetone: 4/1 to 3/1) to give 95.5 mg (71.4%) of colorless amorphous solid.

Workup

  1. customthis was prepared
  2. extractionextracted with CH2Cl2
  3. washThe extracts combined were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (silica gel: 30 g, hexane/acetone: 4/1 to 3/1)

Sources & evidence

ORD record
ord-1742747e932c4f0cbeafcbaf1779f16a
Source dataset
uspto-grants-2001_01
Patent number
US06172067B2

Reaction notes

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