Acetic Acid → HCID 66712082, 화합물

HRID 1262135노트

반응식

HRID 1262135 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 66712082HCID 66712082, 화합물수율 9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bc58d3fb56b54c8e8d91b0d8a4e2f430
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08471005B2

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