HCID 71060717, compound → HCID 71062483, compound

HRID 528974Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][CH:22]=1)[O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12]/[N:13]=[CH:14]/[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:8][CH:7]=1.[N+]([C:26]([CH2:53][CH2:54][CH2:55][CH3:56])=[CH:27][C:28]1[CH:40]=[CH:39][C:31]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])=[CH:30][C:29]=1[C:41]([N:43]1[CH2:52][CH2:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH2:44]1)=[O:42])([O-])=O>>[C:35]([O:34][C:32]([C:31]1[CH:39]=[CH:40][C:28]([C:27]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:13][N:12]([C:9]3[CH:10]=[CH:11][C:6]([O:5][C:4]4[CH:20]=[CH:21][CH:22]=[C:2]([Cl:1])[CH:3]=4)=[CH:7][CH:8]=3)[C:26]=2[CH2:53][CH2:54][CH2:55][CH3:56])=[C:29]([C:41]([N:43]2[CH2:52][CH2:51][C:50]3[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=3)[CH2:44]2)=[O:42])[CH:30]=1)=[O:33])([CH3:36])([CH3:37])[CH3:38]

Participants

Reactant 2

HCID 71060717HCID 71060717, compound

HCID 140641168HCID 140641168, compound

Product 1

HCID 71062483HCID 71062483, compoundYield 45%

Procedure

Following a procedure analogous to that for the synthesis of Intermediate 223E, (E)-ethyl 2-(2-(4-(3-chlorophenoxy)phenyl)hydrazono)acetate (60 mg, 0.19 mmol) and tert-butyl 4-(2-nitrohex-1-enyl)-3-(1,2,3,4-tetrahydroisoquinoline-2-carbonyl)benzoate (88 mg, 0.19 mmol) were converted to the title compound (62 mg, 45%) as a pale yellow oil. 1H NMR (CDCl3, 1:1 mixture of amide rotamers) δ 8.10 (dd, J=8, 2 Hz, 1H), 8.05-8.04 (m, 1H), 7.44-6.83 (m, 13H), 5.02-4.98 (m, 1H), 4.48-4.38 (m, 1H), 4.33-4.28 (m, 2H), 4.18-3.98 (m, 1H), 3.58-3.32 (m, 1H), 2.85-2.50 (m, 4H), 1.61 (s, 9H), 1.29 (t, J=8 Hz, 1.5H), 1.19 (t, J=8 Hz, 1.5H), 1.15-0.81 (m, 4H), 0.65-0.61 (m, 3H); MS(ESI+) m/z 734.3 (M+H)+.

Sources & evidence

ORD record: ord-de09f1bbf12e4565913995bbea1fc3b1
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09346795B2

Reaction notes

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