HCID 67542343, compound → HCID 59383315, compound

HRID 2389955Notes

Reaction equation

HRID 2389955 reaction equation
N1(C2C=CC(C(=O)CN3CCCC3C3C=CC=C(OCCCN4CCOCC4)C=3)=CC=2)C=CN=C1.[N:36]1([C:41]2[CH:46]=[CH:45][C:44]([C:47]3[CH2:48][N:49]4[CH2:69][CH2:68][CH+:67][C:50]4=[C:51]4[C:56]=3[CH:55]=[CH:54][C:53]([O:57][CH2:58][CH2:59][CH2:60][N:61]3[CH2:66][CH2:65][O:64][CH2:63][CH2:62]3)=[CH:52]4)=[CH:43][CH:42]=2)[CH:40]=[CH:39][N:38]=[CH:37]1>>[N:36]1([C:41]2[CH:42]=[CH:43][C:44]([C@H:47]3[C:56]4[C:51](=[CH:52][C:53]([O:57][CH2:58][CH2:59][CH2:60][N:61]5[CH2:62][CH2:63][O:64][CH2:65][CH2:66]5)=[CH:54][CH:55]=4)[C@@H:50]4[CH2:67][CH2:68][CH2:69][N:49]4[CH2:48]3)=[CH:45][CH:46]=2)[CH:40]=[CH:39][N:38]=[CH:37]1.[N:36]1([C:41]2[CH:42]=[CH:43][C:44]([C@H:47]3[C:56]4[C:51](=[CH:52][C:53]([O:57][CH2:58][CH2:59][CH2:60][N:61]5[CH2:62][CH2:63][O:64][CH2:65][CH2:66]5)=[CH:54][CH:55]=4)[C@H:50]4[CH2:67][CH2:68][CH2:69][N:49]4[CH2:48]3)=[CH:45][CH:46]=2)[CH:40]=[CH:39][N:38]=[CH:37]1

Participants

4

Reactant 2

HCID 67542343HCID 67542343, compoundHCID 178420738HCID 178420738, compound

Product 2

HCID 16005497HCID 16005497, compoundYield 4%HCID 59383315HCID 59383315, compoundYield 37%

Procedure

1-(4-Imidazol-1-yl-phenyl)-2-{2-[3-(3-morpholin-4-yl-propoxy)-phenyl]-pyrrolidin-1-yl}-ethanone. Prepared as described in Example 8, Step 1, on a 3.44 mmol scale, to give 1.77 g (>100%) of crude product. MS: exact mass calcd for C28H34N4O3, 474.3; m/z found, 475.5 [M+H]+. Step 2. 6-(4-Imidazol-1-yl-phenyl)-9-(3-morpholin-4-yl-propoxy)-2,3-dihydro-1H-pyrrolo[2,1-a]isoquinolinylium. Prepared as described in Example 17, Step 2, on a 3.43 mmol scale, to give 1.60 g (95%) of crude product. MS: exact mass calcd for C28H31N4O2+, 455.2; m/z found, 455.5 [M]+. Step 3. Prepared as described in Example 17, Step 3, on a 3.43 mmol scale, to give 579 mg (37%) of 48A and 63 mg (4%) of 48B after column chromatography and HPLC. 48A: Cis-6-(4-Imidazol-1-yl-phenyl)-9-(3-morpholin-4-yl-propoxy)-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline. MS: exact mass calcd for C26H33N4O2, 458.3; m/z found, 459.5 [M+H]+. 1H NMR (MeOH-d4): 9.52 (s, 1H), 8.10 (s, 1H), 7.79 (m, 3H), 7.57 (d, J=8.4, 2H), 6.93 (d, J=2.4, 1H), 6.82 (dd, J=1.8, 8.4, 1H), 6.71 (d, J=8.4, 1H), 4.92 (t, J=7.2, 1H), 4.61 (dd, J=4.2, 12.0, 1H), 4.12 (t, J=6.0, 2H), 4.05 (d, J=12.0, 2H), 3.92 (m, 1H), 3.82 (t, J=12.0, 2H), 3.69 (dd, J=4.8, 11.7, 1H), 3.57 (d, J=12.6, 2H), 3.51 (t, J=12.0, 1H), 3.45 (m, 1H), 3.39 (t, J=7.8, 2H),3.18 (m, 2H), 2.87 (m, 1H), 2.30 (br m, 5H). 48B: Trans-6-(4-Imidazol-1-yl-phenyl)-9-(3-morpholin-4-yl-propoxy)-1,2,3,5,6,10b-hexahydro-pyrrolo[2,1-a]isoquinoline

Workup

  1. customPrepared
  2. customto give 1.77 g (>100%) of crude product
  3. customPrepared
  4. customto give 1.60 g (95%) of crude product
  5. customPrepared

Sources & evidence

ORD record
ord-0ced26ab104e4bf0aecd0b33e696083c
Source dataset
uspto-grants-2012_09
Patent number
US08273762B2

Reaction notes

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