HCID 58303866, compound → HCID 50997588, compound

HRID 1404105Notes

Reaction equation

[CH2:1]([NH:8][CH2:9]CC1C2C(=CC=C(F)C=2OC)N(C)C=1)C1C=CC=CC=1.[F:24][C:25]1[C:26]([O:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([CH3:34])[CH:29]=[C:28]2[CH2:35][CH2:36]O>>[F:24][C:25]1[C:26]([O:38][CH2:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[C:27]2[C:31](=[CH:32][CH:33]=1)[N:30]([CH3:34])[CH:29]=[C:28]2[CH2:35][CH2:36][N:8]([CH3:9])[CH3:1]

Participants

Reactant 2

HCID 58303866HCID 58303866, compound

HCID 58303940HCID 58303940, compound

Product 1

HCID 50997588HCID 50997588, compoundYield 72%

Procedure

Following the procedure (step 6, scheme 17) used to prepare compound 17-7, compound 18-1 gave compound 18-2 in 72% yield as a colorless oil, which was converted to the hydrochloride salt. 1H NMR (DMSO-d6, 300 MHz) δ (ppm) (HCl salt): 9.92 (br, 1H), 7.23-7.32 (m, 5H), 7.21 (s, 1H), 7.10 (dd, J=9.1, 4.1 Hz, 1H), 7.04 (dd, J=12.1, 8.8 Hz, 1H), 4.40 (td, J=7.4, 1.6 Hz, 2H), 3.70 (s, 3H), 3.16-3.21 (m, 2H), 3.11 (t, J=7.1 Hz, 2H), 3.00-3.06 (m, 2H), 2.73 (s, 6H). LRMS: calc 340.2 found 341.2 [MH]+.

Sources & evidence

ORD record: ord-e01aed9a69244a5e84f4bf44329fd61a
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912220B2

Reaction notes

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