Acetic Acid → HCID 66712082, compound

HRID 1262135Notes

Reaction equation

HRID 1262135 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.[CH3:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]1[N:24]2[C:19]([CH:20]=[N:21][C:22]([NH:25][C:26]3[CH:31]=[CH:30][C:29]([CH:32]4[CH2:37][CH2:36][NH:35][CH2:34][CH2:33]4)=[CH:28][C:27]=3[O:38][CH3:39])=[N:23]2)=[CH:18][CH:17]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>O1CCCC1>[NH:3]1[CH:4]=[CH:5][N:1]=[C:2]1[CH2:6][N:35]1[CH2:34][CH2:33][CH:32]([C:29]2[CH:30]=[CH:31][C:26]([NH:25][C:22]3[N:21]=[CH:20][C:19]4=[CH:18][CH:17]=[C:16]([C:11]5[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=5[O:9][CH3:8])[N:24]4[N:23]=3)=[C:27]([O:38][CH3:39])[CH:28]=2)[CH2:37][CH2:36]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 249551H-imidazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 66711490HCID 66711490, compound

Product 1

HCID 66712082HCID 66712082, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Imidazole-2-carboxaldehyde (0.011 g, 0.112 mmol) and [7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-(2-methoxy-4-piperidin-4-yl-phenyl)-amine (53 mg, 0.12 mmol) were treated with sodium triacetoxyborohydride (0.033 g, 0.157 mmol) and acetic acid (0.064 mL, 0.112 mmol) in tetrahydrofuran (0.900 mL) at room temperature overnight. The reaction mixture was then concentrated and partitioned between dichloromethane and a saturated aqueous sodium bicarbonate solution. It was dried on NaSO4, filtered and concentrated. The product was isolated by reverse phase hplc (Gilson) to afford {4-[1-(1H-imidazol-2-ylmethyl)-piperidin-4-yl]-2-methoxy-phenyl}-[7-(2-methoxy-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-yl]-amine as a yellow foam (5 mg, 9%). 1H-NMR (CDCl3) δ 9.63 (s, 1H), 8.69 (s, 1H), 8.29 (d, J=8.7 Hz, 1H), 8.00 (d, J=6.2 Hz, 1H), 7.44 (m, 2H), 7.13 (m, 1H), 7.07 (d, J=8.3 Hz, 1H), 7.02 (s, 2H), 6.83 (d, J=4.7 Hz, 1H), 6.73 (m, 2H), 3.89 (s, 3H), 3.84 (s, 3H), 3.71 (s, 2H), 2.97 (d, J=11.4 Hz, 2H), 2.49 (m, 1H), 2.25 (m, 2H), 1.85 (m, 5H); LC/MS (ESI+): 510.2 (M+H).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned between dichloromethane
  3. customIt was dried on NaSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe product was isolated by reverse phase hplc (Gilson)

Sources & evidence

ORD record
ord-bc58d3fb56b54c8e8d91b0d8a4e2f430
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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