1-Butanol → HCID 178478021, compound

HRID 2044908Notes

Reaction equation

HRID 2044908 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:8]([CH2:19][NH2:20])=[CH:7]2.Cl[C:22]1[CH:27]=[CH:26][N:25]=[C:24]2[N:28](C(OC(C)(C)C)=O)[CH:29]=[N:30][C:23]=12.C(N(C(C)C)CC)(C)C.C(O)CCC>CC1C(NC(CN2CCOCC2)=O)=C(C)C=C(OCC2C=CC=CC=2)C=1>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])[C:8]([CH2:19][NH:20][C:22]1[CH:27]=[CH:26][N:25]=[C:24]3[NH:28][CH:29]=[N:30][C:23]=13)=[CH:7]2

Participants

6

Reactant 4

HCID 2631-ButanolHCID 81531DiisopropylethylamineHCID 577080143-Boc-7-chloro-3H-imidazo[4,5-B]pyridineHCID 59264634(8-Chloro-2-(2-chlorophenyl)quinolin-3-yl)methanamine

Product 1

HCID 178478021HCID 178478021, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 2048464-Morpholineacetamide, N-(2,6-dimethyl-4-(phenylmethoxy)phenyl)-Solvent

Procedure

A sealed flask was charged with (8-chloro-2-(2-chlorophenyl)quinolin-3-yl)-methanamine, made in procedure E in A-1216 US PSP, tert-butyl 7-chloro-3H-imidazo[4,5-b]pyridine-3-carboxylate (109 mg, 429 μmol), diisopropylethylamine (0.075 mL, 429 μmol) and 1-butanol (2.0 mL, 21856 μmol). The mixture was subjected to microwave at 180° C. for 120 min. After cooled to room temperature, the mixture was concentrated, and the residue was diluted with MeOH. The solution was purified by HPLC, 25%-45% of B in 35 min. The collected fractions were dissolved in CH2Cl2 and neutralized by washing with aq. NaHCO3, the CH2Cl2 layer was dried, concentrated and gave N-((8-chloro-2-(2-chlorophenyl)-quinolin-3-yl)methyl)-3H-imidazo[4,5-b]pyridin-7-amine (20.2 mg, 15%), 1H NMR (DMSO-d6) δ ppm 12.72 (1 H, s), 8.43 (1 H, s), 8.15 (1 H, s), 8.09 (1 H, d, J=8.0 Hz), 8.05 (1 H, d, J=8.0 Hz), 7.73-7.80 (2 H, m), 7.63-7.70 (4H, m), 7.45 (1 H, s), 6.13 (1 H, d, J=8.0 Hz), 4.60 (2 H, br). Mass Spectrum (ESI) m/e=420.0 (M+1).

Workup

  1. concentrationthe mixture was concentrated
  2. additionthe residue was diluted with MeOH
  3. customThe solution was purified by HPLC, 25%-45% of B in 35 min
  4. dissolutionThe collected fractions were dissolved in CH2Cl2
  5. washby washing with aq. NaHCO3
  6. dry with materialthe CH2Cl2 layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b85f436789a445579ef8e952bac351db
Source dataset
uspto-grants-2013_11
Patent number
US08586739B2

Reaction notes

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