HCID 58303866, compound → HCID 50995812, compound

HRID 1404110Notes

Reaction equation

[CH2:1]([NH:8]CCC1C2C(=CC=C(F)C=2OC)N(C)C=1)C1C=CC=CC=1.[F:24][C:25]1[CH:26]=[C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:28]([O:38][CH3:39])=[C:29]2[C:33]=1[N:32]([CH3:34])[CH:31]=[C:30]2[CH2:35][CH2:36]O>>[F:24][C:25]1[CH:26]=[C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:28]([O:38][CH3:39])=[C:29]2[C:33]=1[N:32]([CH3:34])[CH:31]=[C:30]2[CH2:35][CH2:36][NH:8][CH3:1]

Participants

Reactant 2

HCID 58303866HCID 58303866, compound

HCID 58304003HCID 58304003, compound

Product 1

HCID 50995812HCID 50995812, compoundYield 47%

Procedure

Following the procedure (step 6, scheme 17) used to prepare compound 17-7, compound 22-4 was used as starting material, giving compound 22-5 in 47% yield as a colorless oil, which was converted to the hydrochloride salt. 1H NMR (DMSO-d6, 300 MHz) δ (ppm) (HCl salt): 8.63 (br, 2H), 7.57-7.60 (m, 2H), 7.45 (t, J=7.4 Hz, 2H), 7.30-7.36 (m, 1H), 7.23 (s, 1H), 6.93 (d, J=12.9 Hz, 1H), 3.90 (d, J=1.9 Hz, 3H), 3.36 (s, 3H), 3.16-3.21 (m, 2H), 3.06-3.11 (m, 2H), 2.59 (s, 3H). LRMS: calc 312.2 found 313.1 [MH]+.

Sources & evidence

ORD record: ord-cea73d4e99b54c7a84e99d6888fe4a69
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08912220B2

Reaction notes

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