Acetic Acid → (5-Phenyl-thiazol-2-yl)-(6-piperidin-1-ylmethyl-pyridin-2-yl)-amine

HRID 1355439Notes

Reaction equation

HRID 1355439 reaction equation
[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13]3[N:18]=[C:17]([CH:19]=O)[CH:16]=[CH:15][CH:14]=3)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(O)(=O)C.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C.C(Cl)Cl>[C:1]1([C:7]2[S:11][C:10]([NH:12][C:13]3[CH:14]=[CH:15][CH:16]=[C:17]([CH2:19][N:21]4[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]4)[N:18]=3)=[N:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8082PiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 185068596-(5-Phenyl-thiazol-2-ylamino)-pyridine-2-carbaldehyde

Product 1

HCID 18506805(5-Phenyl-thiazol-2-yl)-(6-piperidin-1-ylmethyl-pyridin-2-yl)-amine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

6-(5-Phenyl-thiazol-2-ylamino)-pyridine-2-carbaldehyde (6-5, 0.025 g, 0.088 mmol) was dissolved in 1 mL dichloroethane. Piperidine (0.014 mL, 0.14 mmol), acetic acid (0.010 mL) and NaBH(OAc)3 (0.030 g, 0.14 mmol) were added. The reaction was stirred at room temperature for 1 h. The reaction was then diluted with CH2Cl2, washed with water and extracted 1× with CH2Cl2. The combined organic phases were dried over Na2SO4, filtered, concentrated. Purification by reverse phase HPLC afforded the titled compound. 1H NMR (CDCl3): δ9.94 (bs, 1H), 7.61 (m, 4H), 7.59 (d, 2H, J=8.0 Hz), 7.41 (t, 2H, J=7.5 Hz), 7.29 (d, 1H, J=7.3 Hz), 7.06 (d, 1H, J=7.4 Hz), 6.77 (d, 1H, J=8.1 Hz), 3.73 (s, 2H), 2.56 (bs, 4H), 1.64 (m, 4H), 1.26 (m, 2H). M+1: 351.1.

Workup

  1. washwashed with water
  2. extractionextracted 1× with CH2Cl2
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by reverse phase HPLC

Sources & evidence

ORD record
ord-2ff4f9399c7546b584fd8f49e058c622
Source dataset
uspto-grants-2003_07
Patent number
US06586423B2

Reaction notes

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