Acetic Acid → HCID 57560985, compound

HRID 1724692Notes

Reaction equation

HRID 1724692 reaction equation
Cl.[CH:2]12[CH2:20][CH:5]([CH:6]([NH:8][C:9]([C:11]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[NH:13][N:12]=3)=[O:10])[CH2:7]1)[CH2:4][NH:3]2.[CH2:21]1[CH:23]([CH:24](O)C#N)[CH2:22]1.C(N(CC)C(C)C)(C)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O>[CH:23]1([CH2:24][N:3]2[CH2:4][CH:5]3[CH2:20][CH:2]2[CH2:7][CH:6]3[NH:8][C:9]([C:11]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][N:12]=2)=[O:10])[CH2:21][CH2:22]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 113893592-Cyclopropyl-2-hydroxyacetonitrileHCID 67273084HCID 67273084, compound

Product 1

HCID 57560985HCID 57560985, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the suspension of N-(2-azabicyclo[2.2.1]hept-5-yl)-1H-indazole-3-carboxamide hydrochloride (0.36 mmol), cyclopropylcarboxaldehyde (0.9 mmol), and N,N-diisopropylethylamine (1.08 mmol), acetic acid (0.43 mmol) was added sodium triacetoxyborohydride (0.61 mmol). The reaction mixture was maintained at rt for 2 h and was poured into water, extracted with 95/5 dichloromethane/methanol (2×30 mL), and the combined extracts were concentrated. The residue was purified by preparative HPLC, thus providing the product in 50% yield. 1H NMR (CD3OD) δ 8.21 (m, 1 H), 7.59 (m, 1 H), 7.45 (m, 1 H), 7.26 (m, 1 H), 4.15 (m, 1 H), 3.83 (m, 1 H), 3.10 (m, 3 H), 2.02 (m, 4 H), 1.37 (m, 2 H), 0.74 (m, 2 H), 0.48 (m, 2 H); LC/MS (EI) tR 2.72 min, m/z 311 (M++1).

Workup

  1. extractionextracted with 95/5 dichloromethane/methanol (2×30 mL)
  2. concentrationthe combined extracts were concentrated
  3. customThe residue was purified by preparative HPLC
  4. customthus providing the product in 50% yield

Sources & evidence

ORD record
ord-8053a0196dfe4deb89466dfc81bb7752
Source dataset
uspto-grants-2009_02
Patent number
US07488737B2

Reaction notes

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