Water → HCID 11948400, compound

HRID 885690Notes

Reaction equation

HRID 885690 reaction equation
[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH:18]([NH2:22])[CH2:19]2)=[N:14]1.[C:23]1([CH2:29][CH2:30][CH:31]=O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].O>ClC(Cl)C.C(O)(=O)C>[CH3:1][O:2][C:3]1[N:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[N:13]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH:18]([NH:22][CH2:31][CH2:30][CH2:29][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:19]2)=[N:14]1

Participants

7

Reactant 4

HCID 962WaterHCID 7707BenzenepropanalHCID 5049666Sodium triacetoxyborohydrideHCID 595606482-(6-Methoxy-[1,5]naphthyridin-4-yl)4,5,6,7-tetrahydro-2H-indazol-5-ylamine

Product 1

HCID 11948400HCID 11948400, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

To a stirring solution of 2-(6-methoxy-[1,5]naphthyridin-4-yl)-4,5,6,7-tetrahydro-2H-indazol-5-ylamine (50 mg, 0.17 mmol) and 3-phenylpropionaldehyde (20 mg, 0.2 mmol) in dichloroethane (2 mL) was added NaB(OAc)3H (37 mg, 0.17 mmol) and acetic acid (2 drops). The reaction mixture was stirred overnight at RT. Water (5 mL) was added, and the aqueous layer was extracted with CH2Cl2 (3×15 mL). The combined organic layers were washed with brine (10 mL), dried (MgSO4), filtered, and concentrated. The crude material was purified on SiO2 (0-5% CH3OH/CH2Cl2) to give 24 mg (36%) of the title compound as a clear oil. MS (ESI): exact mass calculated for C25H27N5O, 413.22; m/z found, 414.5 [M+H]+. 1H NMR (400 MHz, CDCl3): 9.07 (s, 1H), 8.72-8.70 (m, 1H), 8.25-8.23 (m, 1H), 8.08-8.07 (m, 1H), 7.30-7.21 (m, 5H), 7.18-7.16 (m, 1H), 4.09 (s, 3H), 3.06-2.90 (m, 3H), 2.80-2.68 (m, 5H), 2.46-2.40 (m, 1H), 2.19-2.16 (m, 1H), 1.93-1.86 (m, 2H), 1.77-1.67 (m, 1H).

Workup

  1. extractionthe aqueous layer was extracted with CH2Cl2 (3×15 mL)
  2. washThe combined organic layers were washed with brine (10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was purified on SiO2 (0-5% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-f41dbae03c0942af8049baac1d9f63c7
Source dataset
uspto-grants-2012_08
Patent number
US08242275B2

Reaction notes

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