2-Quinolinecarboxaldehyde → HCID 117732478, compound

HRID 718603Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[C:4]2[C:9]([N:10]3[CH2:15][CH2:14][O:13][CH2:12][CH2:11]3)=[CH:8][CH:7]=[N:6][N:5]2[C:16]=1[C:17]1[CH:18]=[CH:19][C:20]([N:23]2[CH2:28][CH2:27][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:25][CH2:24]2)=[N:21][CH:22]=1.[N:36]1[C:45]2[C:40](=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH:39]=[CH:38][C:37]=1[CH:46]=O>>[O:13]1[CH2:12][CH2:11][N:10]([C:9]2[C:4]3[N:5]([C:16]([C:17]4[CH:18]=[CH:19][C:20]([N:23]5[CH2:24][CH2:25][N:26]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:27][CH2:28]5)=[N:21][CH:22]=4)=[C:2]([NH:1][CH2:46][C:37]4[CH:38]=[CH:39][C:40]5[C:45](=[CH:44][CH:43]=[CH:42][CH:41]=5)[N:36]=4)[N:3]=3)[N:6]=[CH:7][CH:8]=2)[CH2:15][CH2:14]1

Participants

Reactant 2

HCID 796192-Quinolinecarboxaldehyde

HCID 117732476HCID 117732476, compound

Product 1

HCID 117732478HCID 117732478, compound

Procedure

Using the procedure described in Example 21, Step C, the title compound was prepared from Compound 23b and 2-quinolinecarbaldehyde. 1H-NMR (400 MHz, CDCl3) δ (ppm): 8.66 (d, J=2.2 Hz, 1H), 8.09 (d, J=8.3 Hz, 1H), 7.97-8.07 (m, 2H), 7.89 (d, J=5.6 Hz, 1H), 7.79 (d, J=8.1 Hz, 1H), 7.70 (ddd, J=8.4, 6.9, 1.3 Hz, 1H), 7.46-7.56 (m, 2H), 6.81 (d, J=9.0 Hz, 1H), 6.03 (d, J=5.6 Hz, 1H), 5.30 (t, J=5.3 Hz, 1H), 4.91 (d, J=5.4 Hz, 2H), 3.81 (s, 8H), 3.49-3.69 (m, 8H), 1.50 (s, 9H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C34H39N9O3: 622.3 (M+H). Found: 622.3.

Sources & evidence

ORD record: ord-b6d1e0a0d9f4448eb998ae26e87076a0
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

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