Tetrahydrofuran → 2-{1-[4-(6-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-benzyl]-piperidin-4-yl}-3H-imidazo[4,5-c]pyridine

HRID 1851267Notes

Reaction equation

HRID 1851267 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]2[NH:15][C:10]3[CH:11]=[N:12][CH:13]=[CH:14][C:9]=3[N:8]=2)[CH2:3][CH2:2]1.[C:16]1([C:22]2[C:23]([C:31]3[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=3)=[N:24][C:25]3[N:26]([N:28]=[CH:29][CH:30]=3)[CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C1COCC1>C(O)(=O)C>[C:16]1([C:22]2[C:23]([C:31]3[CH:32]=[CH:33][C:34]([CH2:35][N:1]4[CH2:2][CH2:3][CH:4]([C:7]5[NH:15][C:10]6[CH:11]=[N:12][CH:13]=[CH:14][C:9]=6[N:8]=5)[CH2:5][CH2:6]4)=[CH:37][CH:38]=3)=[N:24][C:25]3[N:26]([N:28]=[CH:29][CH:30]=3)[CH:27]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 5049666Sodium triacetoxyborohydride3×HCID 223086512-(Piperidin-4-yl)-3H-imidazo[4,5-c]pyridine2×HCID 866306654-(6-Phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Product 1

HCID 687526582-{1-[4-(6-phenyl-pyrazolo[1,5-a]pyrimidin-5-yl)-benzyl]-piperidin-4-yl}-3H-imidazo[4,5-c]pyridine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

252 mg (1.06 mmol) 2-piperidine-4-yl-3H-imidazo[4,5-c]pyridine and 250 mg (0.84 mmol) 4-(6-phenylpyrazolo[1,5-a]pyrimidin-5-yl)benzaldehyde were reacted as described in example 12.0. Additional NaBH(OAc)3 has been added after one, three and five hours (two equivalents each) and the reaction mixture has been stirred overnight at room temperature. Since the reaction has not been complete, 20 mL THF and 10 mL acetic acid were added. Another two equivalents of NaBH(OAc)3 were added. Because after one hour stirring at room temperature the reaction has not changed additional 126 mg 2-piperidine-4-yl-3H-imidazo[4,5-c]pyridine and another two equivalents of NaBH(OAc)3 were added. The reaction has been worked up after stirring at room temperature for 70 hours. After purification 28 mg of the desired material has been obtained.

Workup

  1. stirringBecause after one hour stirring at room temperature the reaction
  2. stirringafter stirring at room temperature for 70 hours
  3. customAfter purification 28 mg of the desired material
  4. customhas been obtained

Sources & evidence

ORD record
ord-4a552c98376c42ea86bd641b2c3fd202
Source dataset
uspto-grants-2015_02
Patent number
US08957064B2

Reaction notes

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